U.S. patent application number 14/237470 was filed with the patent office on 2014-07-24 for fungicidal substituted 1--1h-[1,2,4]triazole compounds.
This patent application is currently assigned to BASF SE. The applicant listed for this patent is Nadege Boudet, Ian Robert Craig, Jochen Dietz, Wassilios Grammenos, Thomas Grote, Egon Haden, Erica May Wilson Lauterwasser, Jan Klaas Lohmann, Bernd Mueller, Richard Riggs. Invention is credited to Nadege Boudet, Ian Robert Craig, Jochen Dietz, Wassilios Grammenos, Thomas Grote, Egon Haden, Erica May Wilson Lauterwasser, Jan Klaas Lohmann, Bernd Mueller, Richard Riggs.
Application Number | 20140206538 14/237470 |
Document ID | / |
Family ID | 46642560 |
Filed Date | 2014-07-24 |
United States Patent
Application |
20140206538 |
Kind Code |
A1 |
Dietz; Jochen ; et
al. |
July 24, 2014 |
Fungicidal substituted 1--1H-[1,2,4]triazole compounds
Abstract
The present invention relates to substituted
1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-alkynyl-ethyl}-1H-[-
1,2,4]triazole compounds of formula I as defined in the
description, and the N-oxides, and salts thereof, processes and
intermediates for preparing these compounds and also to
compositions comprising at least one such compound. The invention
also relates to the use of such compounds and compositions for
combating harmful fungi and seed coated with at least one such
compound.
Inventors: |
Dietz; Jochen; (Karlsruhe,
DE) ; Riggs; Richard; (Mannheim, DE) ; Boudet;
Nadege; (Hemsbach, DE) ; Lohmann; Jan Klaas;
(Lambsheim, DE) ; Craig; Ian Robert;
(Ludwigshafen, DE) ; Haden; Egon; (Speyer, DE)
; Lauterwasser; Erica May Wilson; (Mannheim, DE) ;
Mueller; Bernd; (Frankenthal, DE) ; Grammenos;
Wassilios; (Ludwigshafen, DE) ; Grote; Thomas;
(Wachenheim, DE) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Dietz; Jochen
Riggs; Richard
Boudet; Nadege
Lohmann; Jan Klaas
Craig; Ian Robert
Haden; Egon
Lauterwasser; Erica May Wilson
Mueller; Bernd
Grammenos; Wassilios
Grote; Thomas |
Karlsruhe
Mannheim
Hemsbach
Lambsheim
Ludwigshafen
Speyer
Mannheim
Frankenthal
Ludwigshafen
Wachenheim |
|
DE
DE
DE
DE
DE
DE
DE
DE
DE
DE |
|
|
Assignee: |
BASF SE
Ludwigshafen
DE
|
Family ID: |
46642560 |
Appl. No.: |
14/237470 |
Filed: |
August 14, 2012 |
PCT Filed: |
August 14, 2012 |
PCT NO: |
PCT/EP2012/065852 |
371 Date: |
February 6, 2014 |
Current U.S.
Class: |
504/100 ;
514/383; 548/267.8 |
Current CPC
Class: |
A01N 43/653 20130101;
C07D 249/08 20130101 |
Class at
Publication: |
504/100 ;
548/267.8; 514/383 |
International
Class: |
A01N 43/653 20060101
A01N043/653 |
Foreign Application Data
Date |
Code |
Application Number |
Aug 15, 2011 |
EP |
11177557.3 |
Claims
1-17. (canceled)
18. A compound of formula I ##STR00027## wherein: X.sup.1, X.sup.2
independently of each other are selected from halogen; R.sup.1 is
C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl; wherein the
aliphatic moieties of R.sup.1 may carry 1, 2 or 3 R.sup.a,
independently selected from CN, C.sub.1-C.sub.2-alkoxy and
C.sub.1-C.sub.2-halogenalkoxy; R.sup.2 is C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, phenyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.2-C.sub.4-alkenyl or
phenyl-C.sub.2-C.sub.4-alkynyl; wherein the aliphatic moieties of
R.sup.2 may carry 1, 2, 3 or up to the maximum possible number of
identical or different groups R.sup.a which independently of one
another are selected from the group consisting of halogen, CN,
nitro, phenyl, C.sub.1-C.sub.4-alkoxy and
C.sub.1-C.sub.4-halogenalkoxy, wherein the phenyl may be
substituted by 1, 2, 3, 4 or 5 substituents selected from halogen,
CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl and C.sub.1-C.sub.4-halogenalkoxy;
wherein the cycloalkyl and/or phenyl moieties of R.sup.2 may carry
1, 2, 3, 4, 5 or up to the maximum number of identical or different
groups R.sup.b which independently of one another are selected from
the group consisting of halogen, CN, nitro, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkyl and
C.sub.1-C.sub.4-halogenalkoxy; or an N-oxide or an agriculturally
acceptable salt thereof.
19. The compound of claim 18, wherein X.sup.1 is Cl.
20. The compound of claim 18, wherein X.sup.2 is Cl.
21. The compound of claim 18, wherein R.sup.1 is
C.sub.2-C.sub.4-alkenyl.
22. The compound of claim 18, wherein R.sup.1 is
C.sub.2-C.sub.6-alkynyl.
23. The compound of claim 18, wherein R.sup.1 is unsubstituted.
24. The compound of claim 18, wherein R.sup.2 is
C.sub.1-C.sub.4-alkyl.
25. The compound of claim 18, wherein X.sup.1 and X.sup.2 are Cl,
R.sup.1 is C.XI.CH and R.sup.2 is CH.sub.3, C.sub.2H.sub.5,
CH.sub.2C.XI.CH, CH.sub.2C.sub.6H.sub.5, or
CH.sub.2CH.sub.2CH.sub.3; and compounds wherein X.sup.1 and X.sup.2
are Cl, R.sup.1 is CH.dbd.CH.sub.2 and R.sup.2 is CH.sub.3,
CH.sub.2CH.dbd.CH.sub.2, or CH.sub.2C.XI.CH; and compounds wherein
X.sup.1 and X.sup.2 are Cl, R.sup.1 is C.XI.CCH.sub.3 and R.sup.2
is CH.sub.3, C.sub.2H.sub.5, CH.sub.2CH.dbd.CH.sub.2,
CH.sub.2C.XI.CH or CH.sub.2C(Cl).dbd.CHCl; and compounds wherein
X.sup.1 and X.sup.2 are Cl, R.sup.1 is CH.sub.2C.XI.CH and R.sup.2
is CH.sub.2C.XI.CH.
26. A process for preparing compounds of formula I as defined in
claim 18, which comprises reacting a compound of formula IIIa
##STR00028## wherein Y is F or Cl and X.sup.3 is I or Br, with a
halo-phenole of formula II ##STR00029## under basic conditions;
reacting the resulting compound of formula IVa ##STR00030## with
isopropylmagnesium bromide followed by a reaction with acetyl
chloride; halogenating the resulting compound of formula V
##STR00031## reacting the resulting compound of formula VI
##STR00032## wherein Hal stands for halogen, under basic conditions
with 1H-1,2,4-triazole; reacting the resulting compound of formula
VII ##STR00033## with R.sup.1-M, wherein M is MgBr, MgCl, Li or Na;
and reacting the resulting compound of VIII ##STR00034## under
basic conditions with R.sup.2-LG, wherein LG is a nucleophilically
replaceable leaving group, to obtain compounds of formula I.
27. A process for preparing compounds of formula I as defined in
claim 18, which comprises reacting a compound of formula IIIa
##STR00035## wherein Y is F or Cl and X.sup.3 is I or Br; with
isopropylmagnesium halide followed by a reaction with a compound of
formula IX R.sup.1--COCl; converting the resulting compound of
formula X ##STR00036## wherein Y is F or Cl; under basic conditions
with a halo-phenole of formula II ##STR00037## reacting the
resulting compound of formula Va ##STR00038## with
trimethylsulf(ox)onium halide; reacting the resulting compound of
formula XI ##STR00039## under basic conditions with
1H-1,2,4-triazole; and reacting the resulting compound of formula
VIII ##STR00040## under basic conditions with R.sup.2-LG, wherein
LG is a nucleophilically replaceable leaving group, to obtain
compounds of formula I.
28. A process for preparing compounds of formula I as defined in
claim 18, which comprises reacting a compound of formula XI
##STR00041## under acidic conditions with R.sup.2--OH; reacting the
resulting compound of formula XII ##STR00042## with a halogenating
agent or sulfonating agent; reacting the resulting compound of
formula XIII ##STR00043## wherein LG is a nucleophilically
replaceable leaving group with 1H-1,2,4-triazole, to obtain
compounds I.
29. A compound of formula XII ##STR00044## wherein X.sup.1, X.sup.2
independently of each other are selected from halogen; R.sup.1 is
C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl; wherein the
aliphatic moieties of R.sup.1 may carry 1, 2 or 3 R.sup.a,
independently selected from CN, C.sub.1-C.sub.2-alkoxy and
C.sub.1-C.sub.2-halogenalkoxy; R.sup.2 is C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, phenyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.2-C.sub.4-alkenyl or
phenyl-C.sub.2-C.sub.4-alkynyl; wherein the aliphatic moieties of
R.sup.2 may carry 1, 2, 3 or up to the maximum possible number of
identical or different groups R.sup.a which independently of one
another are selected from the group consisting of halogen, CN,
nitro, phenyl, C.sub.1-C.sub.4-alkoxy and
C.sub.1-C.sub.4-halogenalkoxy, wherein the phenyl may be
substituted by 1, 2, 3, 4 or 5 substituents selected from halogen,
CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4alkoxy,
C.sub.1-C.sub.4-halogenalkyl and C.sub.1-C.sub.4-halogenalkoxy;
wherein the cycloalkyl and/or phenyl moieties of R.sup.2 may carry
1, 2, 3, 4, 5 or up to the maximum number of identical or different
groups R.sup.b which independently of one another are selected from
the group consisting of halogen, CN, nitro, C.sub.1-C.sub.4alkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkyl and
C.sub.1-C.sub.4-halogenalkoxy.
30. A compound of formula VIII or XI ##STR00045## wherein X.sup.1,
X.sup.2 independently of each other are selected from halogen;
R.sup.1 is C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl;
wherein the aliphatic moieties of R.sup.1 may carry 1, 2 or 3
R.sup.a, independently selected from CN, C.sub.1-C.sub.2-alkoxy and
C.sub.1-C.sub.2-halogenalkoxy; with the exception 1) of compounds,
wherein X.sup.1 and X.sup.2 are Cl and R.sup.1 is CH.dbd.CH.sub.2,
CH.dbd.CHCH.sub.3, CH.sub.2CH.dbd.CH.sub.2,
C(CH.sub.3).dbd.CH.sub.2, CH.dbd.CHCH.sub.2CH.sub.3,
CH.sub.2CH.dbd.CHCH.sub.3, CH.sub.2CH.sub.2CH.dbd.CH.sub.2,
CH(CH.dbd.CH.sub.2).sub.2, CH.dbd.C(CH.sub.3).sub.2,
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3,
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3,
CH.dbd.CHC(CH.sub.3).sub.3, C.ident.CCH.sub.3,
C.ident.CCH.sub.2CH.sub.3, CH.sub.2C.ident.CCH.sub.3,
CH.sub.2CH.sub.2C.ident.CH, CH(C.ident.CH).sub.2,
C.ident.CCH.sub.2CH.sub.2CH.sub.3, C.ident.CCH(CH.sub.3).sub.2,
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3,
C.ident.CC(CH.sub.3).sub.3, CH.sub.2C(CH.sub.3).dbd.CH.sub.2,
CH.sub.2C.ident.CH or CH.sub.2C.ident.CCH.sub.2CH.sub.3.
31. An agrochemical composition comprising an auxiliary and at
least one compound of claim 18, an N-oxide or an agriculturally
acceptable salt thereof.
32. The composition according to claim 31, comprising additionally
a further active substance.
33. Seed coated with at least one compound of claim 18, in an
amount of from 0.1 g to 10 kg per 100 kg of seed.
34. A method for controlling phytopathogenic harmful fungi, which
comprises treating the fungi, their habitat or the plants to be
protected against fungal attack, the soil or seeds with a compound
of claim 18.
35. The method of claim 34, wherein X.sup.1 is Cl.
36. The method of claim 34, wherein X.sup.2 is Cl.
37. The method of claim 34, wherein R.sup.1 is
C.sub.2-C.sub.4-alkenyl.
38. The method of claim 34, wherein R.sup.1 is
C.sub.2-C.sub.6-alkynyl.
Description
[0001] The present invention relates to fungicidal
1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-alkynyl/alkenyl-eth-
yl}-1H-[1,2,4]triazole compounds and the N-oxides and the salts
thereof for combating phytopathogenic fungi, and to the use and
methods for combating phytopathogenic fungi and to seeds coated
with at least one such compound. The invention also relates to
processes for preparing these compounds and to compositions
comprising at least one such compound.
[0002] Certain
1-{2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-alkenyloxy-ethyl}-1H-[1,2,4-
]triazole compounds of formula
##STR00001##
wherein R.sup.1 is methyl, ethyl or n-propyl, and their use for
controlling phytopathogenic fungi are known from EP 0 126 430 A2
and U.S. Pat. No. 4,940,720.
[0003] The compounds according to the present invention differ from
those described in the abovementioned publication by the specific
unsaturated alkyl group R.sup.1 as defined herein. DE 3801233 is
directed to microbiocides of the formula I
##STR00002##
wherein R.sup.1 is halogen and R.sup.2 is halogen or methyl,
R.sup.3 is alkyl, haloalkyl, alkoxyalkyl, alkenyl, alkynyl or
cyclopropyl. EP 0 440 950 A2 relates to halogenallyl-azolyl
derivatives. DE 3801233 is directed to microbiocides of the formula
I
##STR00003##
wherein R.sup.1 is halogen and R.sup.2 is halogen or methyl,
R.sup.3 is alkyl, haloalkyl, alkoxyalkyl, alkenyl, alkynyl or
cyclopropyl. CN 101 225 074 relates to compounds of formula
##STR00004##
[0004] J. Agric. Food Chem., vol. 57, 2009, p 4954-4860 relates to
the synthesis and fungicidal evaluation of certain 2-arylphenyl
ether-3-(1H-1,2,4-triazol-1-yl)propan-2-ol derivatives. The
compounds according to the present invention differ from those
described in the abovementioned publications the combination of the
particular 2-[2-halo-4-(4-halogen-phenoxy)-phenyl] group and the
specific R.sup.1 group as defined herein.
[0005] In many cases, in particular at low application rates, the
fungicidal activity of the known fungicidal compounds is
unsatisfactory. Based on this, it was an object of the present
invention to provide compounds having improved activity and/or a
broader activity spectrum against phytopathogenic harmful
fungi.
[0006] This object is achieved by substituted
1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-alkynyl-ethyl}-1H-[-
1,2,4]triazole compounds having good fungicidal activity against
phytopathogenic harmful fungi.
[0007] Accordingly, the present invention relates to the compounds
of formula I:
##STR00005##
wherein: [0008] X.sup.1, X.sup.2 independently of each other are
selected from halogen; [0009] R.sup.1 is C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl; [0010] R.sup.2 is C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, phenyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.2-C.sub.4-alkenyl or
phenyl-C.sub.2-C.sub.4-alkynyl; [0011] wherein the aliphatic
moieties of R.sup.1 and/or R.sup.2 may carry 1, 2, 3 or up to the
maximum possible number of identical or different groups R.sup.a
which independently of one another are selected from: [0012]
R.sup.a halogen, CN, nitro, phenyl, C.sub.1-C.sub.4-alkoxy and
C.sub.1-C.sub.4-halogenalkoxy, [0013] wherein the phenyl may be
substituted by 1, 2, 3, 4 or 5 substituents selected from halogen,
CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl and C.sub.1-C.sub.4-halogenalkoxy;
[0014] wherein the cycloalkyl and/or phenyl moieties of R.sup.2 may
carry 1, 2, 3, 4, 5 or up to the maximum number of identical or
different groups R.sup.b which independently of one another are
selected from: [0015] R.sup.b halogen, CN, nitro,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl and C.sub.1-C.sub.4-halogenalkoxy; and
the N-oxides and the agriculturally acceptable salts thereof.
[0016] The present invention furthermore relates to to the use of
these compounds for combating harmful fungi and seed coated with at
least one such compound and also to compositions comprising at
least one such compound of formula I.
[0017] The present invention furthermore relates to processes for
preparing compounds of formula I and to intermediates such as
compounds of formula Va, VI, VII, VIII, XI, XII and XIII.
[0018] The term "compounds I" refers to compounds of formula I.
Likewise, this terminology applies to all sub-formulae, e.g.
"compounds I.A" refers to compounds of formula I.A or "compounds
XII" refers to compounds of formula XII, etc.
[0019] The compounds I can be obtained by various routes in analogy
to prior art processes known (cf. J. Agric. Food Chem. (2009) 57,
4854-4860; EP 0 275 955 A1; DE 40 03 180 A1; EP 0 113 640 A2; EP 0
126 430 A2) and by the synthesis routes shown in the following
schemes and in the experimental part of this application.
[0020] In a first process, for example, halo-phenoles II wherein
X.sup.1 and X.sup.2 as defined herein in, are reacted, in a first
step, with derivatives IIIa
##STR00006##
wherein X.sup.3 stands for I or Br, in particular bromo derivatives
III wherein Y is F or Cl, preferably in the presence of a base.
Thereafter, the resulting compounds IVa, in particular IV (wherein
X.sup.3 is Br), are then transformed into Grignard reagents by the
reaction with transmetallation reagents such as isopropylmagnesium
halides and subsequently reacted with acetyl chloride preferably
under anhydrous conditions and optionally in the presence of a
catalyst such as CuCl, AlCl.sub.3, LiCl and mixtures thereof, to
obtain acetophenones V. These compounds V can be halogenated e.g.
with bromine or chlorine preferably in an organic solvent such as
diethyl ether, methyl tert.-butyl ether (MTBE), methanol or acetic
acid. The resulting compounds VI, wherein "Hal" stands for
"halogen" such as e.g. Br or Cl, can subsequently reacted with
1H-1,2,4-triazole preferably in the presence of a solvent such as
tetrahydrofuran (THF), dimethylormamide (DMF), toluene and in the
presence of a base such as potassium carbonate, sodium hydroxide or
sodium hydride to obtain compounds VII. These triazole compounds
VII are reacted with a Grignard reagent R.sup.1-M wherein R.sup.1
is as defined herein and M is MgBr, MgCl, Li or Na (e.g.
phenylalkyl-MgBr or an organolithium reagent phenylalkyl-Li),
preferably under anhydrous conditions to obtain compounds VIII.
Optionally, a Lewis acid such as LaCl.sub.3x2LiCl or
MgBr.sub.2xOEt.sub.2 can be used. These compounds VIII are reacted
with R.sup.2-LG, wherein R.sup.1 is as defined above and LG
represents a nucleophilically replaceable leaving group such as
halogen, alkylsulfonyl, alkylsulfonyloxy and arylsulfonyloxy,
preferably chloro, bromo or iodo, particularly preferably bromo,
preferably in the presence of a base, such as for example, NaH in a
suitable solvent such as THF, to form compounds I. The preparation
of compounds I can be illustrated by the following scheme:
##STR00007##
[0021] In a second process to obtain compounds I, derivatives IIIa,
in particular bromo derivatives III, in a first step, are reacted
with e.g. isopropylmagnesium bromide followed by an acyl chloride
agent IX wherein R.sup.1 is as defined herein (e.g. acetyl
chloride) preferably under anhydrous conditions and optionally in
the presence of a catalyst such as CuCl, AlCl.sub.3, LiCl and
mixtures thereof, to obtain compounds X. Alternatively, compounds
IIIc
##STR00008##
e.g. 1,3-dichlorobenzene of formula IIIb can be reacted with an
acyl chloride agent IX wherein R.sup.1 is as defined above (e.g.
acetyl chloride) preferably in the presence of a catalyst such as
AlCl.sub.3. Then, ketones X are reacted with phenoles II preferably
in the presence of a base to obtain compounds Va. Compounds Va may
also be obtained in analogy to the first process described for
compounds V.
[0022] Thereafter, intermediates Va are reacted with
trimethylsulf(ox)onium halides preferably iodide preferably in the
presence of a base such as sodium hydroxide. Thereafter, the
epoxides XI are reacted with 1H-1,2,4-triazole preferably in the
presence of a base such as potassium carbonate and preferably in
the presence of an organic solvent such as DMF to obtain compounds
VIII. These compounds VIII are reacted with R.sup.2-LG, wherein
R.sup.2 is as defined above and LG represents a nucleophilically
replaceable leaving group such as halogen, alkylsulfonyl,
alkylsulfonyloxy and arylsulfonyloxy, preferably chloro, bromo or
iodo, particularly preferably bromo, preferably in the presence of
a base to form compounds I, which can subsequently be alkylated as
described above. The preparation of compounds I can be illustrated
by the following scheme:
##STR00009##
In a third process, the epoxide ring of intermediates XI which may
be obtained according to the second process described herein is
cleaved by reaction with alcohols R.sup.2OH preferably under acidic
conditions. Thereafter, the resulting compounds XII are reacted
with halogenating agents or sulfonating agents such as PBr.sub.3,
PCl.sub.3, mesyl chloride, tosyl chloride or thionyl chloride to
obtain compounds XIII wherein LG is a nucleophilically replaceable
leaving group such as halogen, alkylsulfonyl, alkylsulfonyloxy and
arylsulfonyloxy, preferably chloro, bromo or iodo, particularly
preferably bromo or alkylsulfonyl. Then compounds XIII are reacted
with 1H-1,2,4-triazole to obtain compounds
[0023] I. The preparation of compounds I can be illustrated by the
following scheme:
##STR00010##
[0024] If individual compounds I cannot be obtained by the routes
described above, they can be prepared by derivatization of other
compounds I.
[0025] The N-oxides may be prepared from the compounds I according
to conventional oxidation methods, e.g. by treating compounds I
with an organic peracid such as metachloroperbenzoic acid (cf. WO
03/64572 or J. Med. Chem. 38(11), 1892-903, 1995); or with
inorganic oxidizing agents such as hydrogen peroxide (cf. J.
Heterocyc. Chem. 18(7), 1305-8, 1981) or oxone (cf. J. Am. Chem.
Soc. 123(25), 5962-5973, 2001). The oxidation may lead to pure
mono-N-oxides or to a mixture of different N-oxides, which can be
separated by conventional methods such as chromatography.
[0026] If the synthesis yields mixtures of isomers, a separation is
generally not necessarily required since in some cases the
individual isomers can be interconverted during workup for use or
during application (e.g. under the action of light, acids or
bases). Such conversions may also take place after use, e.g. in the
treatment of plants in the treated plant, or in the harmful fungus
to be controlled.
[0027] In the following, the intermediate compounds are further
described. A skilled person will readily understand that the
preferences for the substituents given herein in connection with
compounds I apply for the intermediates accordingly. Thereby, the
substituents in each case have independently of each other or more
preferably in combination the meanings as defined herein.
The present invention also relates to novel compounds of formula
Va
##STR00011##
wherein the variables R.sup.1, X.sup.1, X.sup.2 are as defined and
preferably defined for formula I herein. In specific embodiments of
compounds Va according to the present invention, the substituents
R.sup.1, X.sup.1, X.sup.2 are as defined in tables 1 to 148 and
148a to 148z and 148aa to 148jj and 149 to 296 and 296a to 296z and
296aa to 296jj for compounds I, wherein the substituents are
specific embodiments independently of each other or in any
combination.
[0028] A further embodiment of the present invention are novel
compounds of formula VI:
##STR00012##
[0029] Wherein the variables X.sup.1, X.sup.2 are as defined and
preferably defined for formula I herein, and wherein Hal stands for
halogen, in particular Cl or Br. According to one preferred
embodiment Hal in compounds VI stands for Br.
[0030] A further embodiment of the present invention are novel
compounds of formula VII:
##STR00013##
Wherein the variables X.sup.1, X.sup.2 are as defined and
preferably defined for formula I herein. In specific embodiments of
compounds VII according to the present invention, the substituents
X.sup.1, X.sup.2 are as defined in tables 1 to 148 and 148a to 148z
and 148aa to 148jj and 149 to 296 and 296a to 296z and 296aa to
296jj, wherein the substituents are specific embodiments
independently of each other or in any combination.
[0031] A further embodiment of the present invention are novel
compounds of formula VIII:
##STR00014##
Wherein the variables X.sup.1, X.sup.2 and R.sup.1 are as defined
and preferably defined for formula I herein, with the exception
[0032] 1) of compounds, wherein X.sup.1 and X.sup.2 are Cl and
R.sup.1 is CH.dbd.CH.sub.2, CH.dbd.CHCH.sub.3,
CH.sub.2CH.dbd.CH.sub.2, C(CH.sub.3).dbd.CH.sub.2,
CH.dbd.CHCH.sub.2CH.sub.3, CH.sub.2CH.dbd.CHCH.sub.3,
CH.sub.2CH.sub.2CH.dbd.CH.sub.2, CH(CH.dbd.CH.sub.2).sub.2,
CH.dbd.C(CH.sub.3).sub.2, CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3,
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3,
CH.dbd.CHC(CH.sub.3).sub.3, CCH, C.ident.CCH.sub.3,
C.ident.CCH.sub.2CH.sub.3, CH.sub.2C.ident.CCH.sub.3,
CH.sub.2CH.sub.2C.ident.CH, CH(C.ident.CH).sub.2,
C.ident.CCH.sub.2CH.sub.2CH.sub.3, C.ident.CCH(CH.sub.3).sub.2,
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3,
C.ident.CC(CH.sub.3).sub.3, CH.sub.2C(CH.sub.3).dbd.CH.sub.2,
CH.sub.2C.ident.CH, CH.sub.2C.ident.CCH.sub.2CH.sub.3,
CH.sub.2C(Br).dbd.CHBr or CH.sub.2CCl.dbd.CHCl; and
[0033] 2) of compounds, wherein X.sup.1 and X.sup.2 are Cl and
R.sup.1 is a moiety AR.sup.1
##STR00015##
wherein: [0034] # denotes the attachment point to formula VIII,
[0035] X is C.sub.2-C.sub.4-alkynediyl; [0036] R is halogen, CN,
nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl or C.sub.1-C.sub.4-halogenalkoxy;
[0037] n is an integer and is 0, 1, 2, 3, 4 or 5; and
[0038] 3) of compounds, wherein X.sup.1 and X.sup.2 are Cl and
R.sup.1 is CH.dbd.CHC.sub.6H.sub.5,
CH.dbd.CH(4-Cl--C.sub.6H.sub.4),
CH.dbd.CH(2,4-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(2,6-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(4-CH.sub.3--C.sub.6H.sub.4),
CH.dbd.CH(4-OCH.sub.3--C.sub.6H.sub.4),
CH.dbd.CH(3,4-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(2-F--C.sub.6H.sub.4),
CH.dbd.CH(4-NO.sub.2--C.sub.6H.sub.4),
CH.dbd.CH(2-NO.sub.2--C.sub.6H.sub.4),
CH.dbd.CH(2-Cl--C.sub.6H.sub.4), CH.dbd.CH(4-F--C.sub.6H.sub.4) or
CH.dbd.CH(4-C.sub.2H.sub.5--C.sub.6H.sub.4).
According to one embodiment, the variables X.sup.1, X.sup.2 and
R.sup.1 are as defined and preferably defined for formula I herein,
with the exception [0039] 1) of compounds, wherein X.sup.1 and
X.sup.2 are Cl and R.sup.1 is C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl; wherein R.sup.1 are unsubstituted or carry
1, 2, 3 or 4 CN substituents; and [0040] 2) of compounds, wherein
X.sup.1 and X.sup.2 are Cl and R.sup.1 is CH.sub.2C(Br).dbd.CHBr or
CH.sub.2CCl.dbd.CHCl; and [0041] 3) of compounds, wherein X.sup.1
and X.sup.2 are Cl and R.sup.1 is a moiety AR.sup.1
##STR00016##
[0041] wherein: [0042] # denotes the attachment point to formula
VIII, [0043] X is C.sub.2-C.sub.4-alkynediyl; [0044] R is halogen,
CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl or C.sub.1-C.sub.4-halogenalkoxy;
[0045] n is an integer and is 0, 1, 2, 3, 4 or 5; and [0046] 4) of
compounds, wherein X.sup.1 and X.sup.2 are Cl and R.sup.1 is
CH.dbd.CHC.sub.6H.sub.5, CH.dbd.CH(4-Cl--C.sub.6H.sub.4),
CH.dbd.CH(2,4-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(2,6-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(4-CH.sub.3--C.sub.6H.sub.4),
CH.dbd.CH(4-OCH.sub.3--C.sub.6H.sub.4),
CH.dbd.CH(3,4-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(2-F--C.sub.6H.sub.4),
CH.dbd.CH(4-NO.sub.2--C.sub.6H.sub.4),
CH.dbd.CH(2-NO.sub.2--C.sub.6H.sub.4),
CH.dbd.CH(2-Cl--C.sub.6H.sub.4), CH.dbd.CH(4-F--C.sub.6H.sub.4) or
CH.dbd.CH(4-C.sub.2H.sub.5--C.sub.6H.sub.4).
[0047] According to one embodiment, in compounds VIII X.sup.1 and
X.sup.2 are not both Cl.
[0048] According to another embodiment, in compounds VIII R.sup.1
is C.sub.2-C.sub.6-alkynyl, that is unsubstituted or that may carry
1, 2, 3 or up to the maximum possible number of identical or
different groups R.sup.a which independently of one another are
selected from halogen, CN, nitro, C.sub.1-C.sub.2-alkoxy and
C.sub.1-C.sub.2-halogenalkoxy, taking into account the above
disclaimer.
[0049] Compounds VIII are also suitable as fungicides as described
herein for compounds of formula I. Specific preferred compounds
VIII are the following C-1 to C-156, wherein each compound
corresponds to one line of table C:
TABLE-US-00001 TABLE C Compounds C-1 to C-156 of formula VIII line
X.sup.1 X.sup.2 R.sup.1 C-1 Cl F CH.dbd.CH.sub.2 C-2 F Cl
CH.dbd.CH.sub.2 C-3 F F CH.dbd.CH.sub.2 C-4 Cl F
CH.sub.2CH.dbd.CH.sub.2 C-5 F CI CH.sub.2CH.dbd.CH.sub.2 C-6 F F
CH.sub.2CH.dbd.CH.sub.2 C-7 Cl F CH.sub.2CH.dbd.CHCH.sub.3 C-8 F Cl
CH.sub.2CH.dbd.CHCH.sub.3 C-9 F F CH.sub.2CH.dbd.CHCH.sub.3 C-10 Cl
Cl CH.sub.2CH.dbd.CHF C-11 Cl F CH.sub.2CH.dbd.CHF C-12 F Cl
CH.sub.2CH.dbd.CHF C-13 F F CH.sub.2CH.dbd.CHF C-14 Cl Cl
CH.sub.2CH.dbd.CHCl C-15 Cl F CH.sub.2CH.dbd.CHCl C-16 F Cl
CH.sub.2CH.dbd.CHCl C-17 F F CH.sub.2CH.dbd.CHCl C-18 Cl F
CH.sub.2C(CH.sub.3).dbd.CH.sub.2 C-19 F Cl
CH.sub.2C(CH.sub.3).dbd.CH.sub.2 C-20 F F
CH.sub.2C(CH.sub.3).dbd.CH.sub.2 C-21 Cl Cl
CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 C-22 Cl F
CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 C-23 F Cl
CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 C-24 F F
CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 C-25 Cl Cl
CH.sub.2C(CH.sub.3).dbd.CHF C-26 Cl F CH.sub.2C(CH.sub.3).dbd.CHF
C-27 F Cl CH.sub.2C(CH.sub.3).dbd.CHF C-28 F F
CH.sub.2C(CH.sub.3).dbd.CHF C-29 Cl Cl CH.sub.2C(CH.sub.3).dbd.CHCl
C-30 Cl F CH.sub.2C(CH.sub.3).dbd.CHCl C-31 F Cl
CH.sub.2C(CH.sub.3).dbd.CHCl C-32 F F CH.sub.2C(CH.sub.3).dbd.CHCl
C-33 Cl F CH.sub.2C.ident.CH C-34 F Cl CH.sub.2C.ident.CH C-35 F F
CH.sub.2C.ident.CH C-36 Cl F CH.sub.2C.ident.CCH.sub.3 C-37 F Cl
CH.sub.2C.ident.CCH.sub.3 C-38 F F CH.sub.2C.ident.CCH.sub.3 C-39
Cl Cl CH.sub.2C.ident.CCF.sub.3 C-40 Cl F CH.sub.2C.ident.CCF.sub.3
C-41 F Cl CH.sub.2C.ident.CCF.sub.3 C-42 F F
CH.sub.2C.ident.CCF.sub.3 C-43 Cl Cl CH.sub.2C.ident.CCl C-44 Cl F
CH.sub.2C.ident.CCl C-45 F Cl CH.sub.2C.ident.CCl C-46 F F
CH.sub.2C.ident.CCl C-47 Cl Cl CH(CH.sub.3)C.ident.CH C-48 Cl F
CH(CH.sub.3)C.ident.CH C-49 F Cl CH(CH.sub.3)C.ident.CH C-50 F F
CH(CH.sub.3)C.ident.CH C-51 Cl Cl CH(CH.sub.3)C.ident.CCl C-52 Cl F
CH(CH.sub.3)C.ident.CCl C-53 F Cl CH(CH.sub.3)C.ident.CCl C-54 F F
CH(CH.sub.3)C.ident.CCl C-55 Cl F CH.dbd.CH--C.sub.6H.sub.5 C-56 F
Cl CH.dbd.CH--C.sub.6H.sub.5 C-57 F F CH.dbd.CH--C.sub.6H.sub.5
C-58 Cl Cl C.ident.C--C.sub.6H.sub.5 C-59 Cl F
C.ident.C--C.sub.6H.sub.5 C-60 F Cl C.ident.C--C.sub.6H.sub.5 C-61
F F C.ident.C--C.sub.6H.sub.5 C-62 Cl Cl
CH.sub.2--C.ident.C--C.sub.6H.sub.5 C-63 Cl F
CH.sub.2--C.ident.C--C.sub.6H.sub.5 C-64 F Cl
CH.sub.2--C.ident.C--C.sub.6H.sub.5 C-65 F F
CH.sub.2--C.ident.C--C.sub.6H.sub.5 C-66 Cl F CH.dbd.CHCH.sub.3
C-67 F Cl CH.dbd.CHCH.sub.3 C-68 F F CH.dbd.CHCH.sub.3 C-69 Cl F
C(CH.sub.3).dbd.CH.sub.2 C-70 F Cl C(CH.sub.3).dbd.CH.sub.2 C-71 F
F C(CH.sub.3).dbd.CH.sub.2 C-72 Cl F CH.dbd.CHCH.sub.2CH.sub.3 C-73
F Cl CH.dbd.CHCH.sub.2CH.sub.3 C-74 F F CH.dbd.CHCH.sub.2CH.sub.3
C-75 Cl F CH.sub.2CH.sub.2CH.dbd.CH.sub.2 C-76 F Cl
CH.sub.2CH.sub.2CH.dbd.CH.sub.2 C-77 F F
CH.sub.2CH.sub.2CH.dbd.CH.sub.2 C-78 Cl F CH(CH.dbd.CH.sub.2).sub.2
C-79 F Cl CH(CH.dbd.CH.sub.2).sub.2 C-80 F F
CH(CH.dbd.CH.sub.2).sub.2 C-81 Cl F CH.dbd.C(CH.sub.3).sub.2 C-82 F
Cl CH.dbd.C(CH.sub.3).sub.2 C-83 F F CH.dbd.C(CH.sub.3).sub.2 C-84
Cl F CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3 C-85 F Cl
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3 C-86 F F
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3 C-87 Cl F
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 C-88 F Cl
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 C-89 F F
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 C-90 Cl F
CH.dbd.CHC(CH.sub.3).sub.3 C-91 F Cl CH.dbd.CHC(CH.sub.3).sub.3
C-92 F F CH.dbd.CHC(CH.sub.3).sub.3 C-93 Cl F C.ident.CH C-94 F Cl
C.ident.CH C-95 F F C.ident.CH C-96 Cl F C.ident.CCH.sub.3 C-97 F
Cl C.ident.CCH.sub.3 C-98 F F C.ident.CCH.sub.3 C-99 Cl F
C.ident.CCH.sub.2CH.sub.3 C-100 F Cl C.ident.CCH.sub.2CH.sub.3
C-101 F F C.ident.CCH.sub.2CH.sub.3 C-102 Cl F
CH.sub.2CH.sub.2C.ident.CH C-103 F Cl CH.sub.2CH.sub.2C.ident.CH
C-104 F F CH.sub.2CH.sub.2C.ident.CH C-105 Cl F
CH(C.ident.CH).sub.2 C-106 F Cl CH(C.ident.CH).sub.2 C-107 F F
CH(C.ident.CH).sub.2 C-108 Cl F C.ident.CCH.sub.2CH.sub.2CH.sub.3
C-109 F Cl C.ident.CCH.sub.2CH.sub.2CH.sub.3 C-110 F F
C.ident.CCH.sub.2CH.sub.2CH.sub.3 C-111 Cl F
C.ident.CCH(CH.sub.3).sub.2 C-112 F Cl C.ident.CCH(CH.sub.3).sub.2
C-113 F F C.ident.CCH(CH.sub.3).sub.2 C-114 Cl F
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3 C-115 F Cl
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3 C-116 F F
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3 C-117 Cl F
C.ident.CC(CH.sub.3).sub.3 C-118 F Cl C.ident.CC(CH.sub.3).sub.3
C-119 F F C.ident.CC(CH.sub.3).sub.3 C-120 Cl F
CH.sub.2C.ident.CCH.sub.2CH.sub.3 C-121 F Cl
CH.sub.2C.ident.CCH.sub.2CH.sub.3 C-122 F F
CH.sub.2C.ident.CCH.sub.2CH.sub.3 C-123 Cl F
CH.dbd.CH-(4-F--C.sub.6H.sub.4) C-124 F Cl
CH.dbd.CH-(4-F--C.sub.6H.sub.4) C-125 F F
CH.dbd.CH-(4-F--C.sub.6H.sub.4) C-126 Cl F
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4) C-127 F Cl
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4) C-128 F F
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4) C-129 Cl Cl
CH.dbd.CHCH.sub.2OCH.sub.3 C-130 Cl F CH.dbd.CHCH.sub.2OCH.sub.3
C-131 F Cl CH.dbd.CHCH.sub.2OCH.sub.3 C-132 F F
CH.dbd.CHCH.sub.2OCH.sub.3 C-133 Cl Cl CH.dbd.CCl.sub.2 C-134 Cl F
CH.dbd.CCl.sub.2 C-135 F Cl CH.dbd.CCl.sub.2 C-136 F F
CH.dbd.CCl.sub.2 C-137 Cl Cl CH.dbd.CHOCH.sub.3 C-138 Cl F
CH.dbd.CHOCH.sub.3 C-139 F Cl CH.dbd.CHOCH.sub.3 C-140 F F
CH.dbd.CHOCH.sub.3 C-141 Cl Cl CH.sub.2C.ident.CCH(CH.sub.3).sub.2
C-142 Cl F CH.sub.2C.ident.CCH(CH.sub.3).sub.2 C-143 F Cl
CH.sub.2C.ident.CCH(CH.sub.3).sub.2 C-144 F F
CH.sub.2C.ident.CCH(CH.sub.3).sub.2 C-145 Cl Cl
CH.sub.2C.ident.CC(CH.sub.3).sub.3 C-146 Cl F
CH.sub.2C.ident.CC(CH.sub.3).sub.3 C-147 F Cl
CH.sub.2C.ident.CC(CH.sub.3).sub.3 C-148 F F
CH.sub.2C.ident.CC(CH.sub.3).sub.3 C-149 Cl Cl
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 C-150 Cl F
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 C-151 F Cl
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 C-152 F F
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 C-153 Cl Cl
CH.sub.2C(Cl).dbd.CHCl C-154 Cl F CH.sub.2C(Cl).dbd.CHCl C-155 F Cl
CH.sub.2C(Cl).dbd.CHCl C-156 F F CH.sub.2C(Cl).dbd.CHCl
[0050] A further embodiment of the present invention are novel
compounds of formula XI:
##STR00017##
wherein the variables X.sup.1, X.sup.2 and R.sup.1 are as defined
and preferably defined for formula I herein, with the exception 1)
of compounds, wherein X.sup.1 and X.sup.2 are Cl and R.sup.1 is
CH.dbd.CH.sub.2, CH.dbd.CHCH.sub.3, CH.sub.2CH.dbd.CH.sub.2,
C(CH.sub.3).dbd.CH.sub.2, CH.dbd.CHCH.sub.2CH.sub.3,
CH.sub.2CH.dbd.CHCH.sub.3, CH.sub.2CH.sub.2CH.dbd.CH.sub.2,
CH(CH.dbd.CH.sub.2).sub.2, CH.dbd.C(CH.sub.3).sub.2,
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3,
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3,
CH.dbd.CHC(CH.sub.3).sub.3, CCH, C.ident.CCH.sub.3,
C.ident.CCH.sub.2CH.sub.3, CH.sub.2C.ident.CCH.sub.3,
CH.sub.2CH.sub.2CCH, CH(C.ident.CH).sub.2,
C.ident.CCH.sub.2CH.sub.2CH.sub.3, C.ident.CCH(CH.sub.3).sub.2,
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3,
C.ident.CC(CH.sub.3).sub.3, CH.sub.2C(CH.sub.3).dbd.CH.sub.2,
CH.sub.2CCH, CH.sub.2C.ident.CCH.sub.2CH.sub.3,
CH.sub.2C(Br).dbd.CHBr or CH.sub.2CCl.dbd.CHCl; and [0051] 2) of
compounds, wherein X.sup.1 and X.sup.2 are Cl and R.sup.1 is a
moiety AR.sup.1
##STR00018##
[0051] wherein: [0052] # denotes the attachment point to formula
VIII, [0053] X is C.sub.2-C.sub.4-alkynediyl; [0054] R is halogen,
CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl or C.sub.1-C.sub.4-halogenalkoxy;
[0055] n is an integer and is 0, 1, 2, 3, 4 or 5; and [0056] 3) of
compounds, wherein X.sup.1 and X.sup.2 are Cl and R.sup.1 is
CH.dbd.CHC.sub.6H.sub.5, CH.dbd.CH(4-Cl--C.sub.6H.sub.4),
CH.dbd.CH(2,4-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(2,6-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(4-CH.sub.3--C.sub.6H.sub.4),
CH.dbd.CH(4-OCH.sub.3--C.sub.6H.sub.4),
CH.dbd.CH(3,4-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(2-F--C.sub.6H.sub.4),
CH.dbd.CH(4-NO.sub.2--C.sub.6H.sub.4),
CH.dbd.CH(2-NO.sub.2--C.sub.6H.sub.4),
CH.dbd.CH(2-Cl--C.sub.6H.sub.4), CH.dbd.CH(4-F--C.sub.6H.sub.4) or
CH.dbd.CH(4-C.sub.2H.sub.5--C.sub.6H.sub.4).
[0057] According to one embodiment, the variables X.sup.1, X.sup.2
and R.sup.1 are as defined and preferably defined for formula I
herein, with the exception [0058] 1) of compounds, wherein X.sup.1
and X.sup.2 are Cl and R.sup.1 is C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl; wherein R.sup.1 are unsubstituted or carry
1, 2, 3 or 4 CN substituents; and [0059] 2) of compounds, wherein
X.sup.1 and X.sup.2 are Cl and R.sup.1 is CH.sub.2C(Br).dbd.CHBr or
CH.sub.2CCl.dbd.CHCl; and [0060] 3) of compounds, wherein X.sup.1
and X.sup.2 are Cl and R.sup.1 is a moiety AR.sup.1
##STR00019##
[0060] wherein: [0061] # denotes the attachment point to formula
VIII, [0062] X is C.sub.2-C.sub.4-alkynediyl; [0063] R is halogen,
CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl or C.sub.1-C.sub.4-halogenalkoxy;
[0064] n is an integer and is 0, 1, 2, 3, 4 or 5; and [0065] 4) of
compounds, wherein X.sup.1 and X.sup.2 are Cl and R.sup.1 is
CH.dbd.CHC.sub.6H.sub.5, CH.dbd.CH(4-Cl--C.sub.6H.sub.4),
CH.dbd.CH(2,4-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(2,6-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(4-CH.sub.3--C.sub.6H.sub.4),
CH.dbd.CH(4-OCH.sub.3--C.sub.6H.sub.4),
CH.dbd.CH(3,4-Cl.sub.2--C.sub.6H.sub.3),
CH.dbd.CH(2-F--C.sub.6H.sub.4),
CH.dbd.CH(4-NO.sub.2--C.sub.6H.sub.4),
CH.dbd.CH(2-NO.sub.2--C.sub.6H.sub.4),
CH.dbd.CH(2-Cl--C.sub.6H.sub.4), CH.dbd.CH(4-F--C.sub.6H.sub.4) or
CH.dbd.CH(4-C.sub.2H.sub.5--C.sub.6H.sub.4).
[0066] According to one embodiment, in compounds VIII X.sup.1 and
X.sup.2 are not both Cl.
[0067] In specific embodiments of compounds XI according to the
present invention, the substituents X.sup.1, X.sup.2 and R.sup.1
are as defined in tables 1 to 148 and 148a to 148z and 148aa to
148jj and 149 to 296 and 296a to 296z and 296aa to 296jj, wherein
the substituents are specific embodiments independently of each
other or in any combination.
[0068] Specific preferred compounds XI are the following D-1 to
D-156, wherein each compound corresponds to one line of table
D:
TABLE-US-00002 TABLE D Compounds D-1 to D-156 of formula XI line
X.sup.1 X.sup.2 R.sup.1 D-1 Cl F CH.dbd.CH.sub.2 D-2 F Cl
CH.dbd.CH.sub.2 D-3 F F CH.dbd.CH.sub.2 D-4 Cl F
CH.sub.2CH.dbd.CH.sub.2 D-5 F Cl CH.sub.2CH.dbd.CH.sub.2 D-6 F F
CH.sub.2CH.dbd.CH.sub.2 D-7 Cl F CH.sub.2CH.dbd.CHCH.sub.3 D-8 F Cl
CH.sub.2CH.dbd.CHCH.sub.3 D-9 F F CH.sub.2CH.dbd.CHCH.sub.3 D-10 Cl
Cl CH.sub.2CH.dbd.CHF D-11 Cl F CH.sub.2CH.dbd.CHF D-12 F Cl
CH.sub.2CH.dbd.CHF D-13 F F CH.sub.2CH.dbd.CHF D-14 Cl Cl
CH.sub.2CH.dbd.CHCl D-15 Cl F CH.sub.2CH.dbd.CHCl D-16 F Cl
CH.sub.2CH.dbd.CHCl D-17 F F CH.sub.2CH.dbd.CHCl D-18 Cl F
CH.sub.2C(CH.sub.3).dbd.CH.sub.2 D-19 F Cl
CH.sub.2C(CH.sub.3).dbd.CH.sub.2 D-20 F F
CH.sub.2C(CH.sub.3).dbd.CH.sub.2 D-21 Cl Cl
CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 D-22 Cl F
CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 D-23 F Cl
CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 D-24 F F
CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 D-25 Cl Cl
CH.sub.2C(CH.sub.3).dbd.CHF D-26 Cl F CH.sub.2C(CH.sub.3).dbd.CHF
D-27 F Cl CH.sub.2C(CH.sub.3).dbd.CHF D-28 F F
CH.sub.2C(CH.sub.3).dbd.CHF D-29 Cl Cl CH.sub.2C(CH.sub.3).dbd.CHCl
D-30 Cl F CH.sub.2C(CH.sub.3).dbd.CHCl D-31 F Cl
CH.sub.2C(CH.sub.3).dbd.CHCl D-32 F F CH.sub.2C(CH.sub.3).dbd.CHCl
D-33 Cl F CH.sub.2C.ident.CH D-34 F Cl CH.sub.2C.ident.CH D-35 F F
CH.sub.2C.ident.CH D-36 Cl F CH.sub.2C.ident.CCH.sub.3 D-37 F Cl
CH.sub.2C.ident.CCH.sub.3 D-38 F F CH.sub.2C.ident.CCH.sub.3 D-39
Cl Cl CH.sub.2C.ident.CCF.sub.3 D-40 Cl F CH.sub.2C.ident.CCF.sub.3
D-41 F Cl CH.sub.2C.ident.CCF.sub.3 D-42 F F
CH.sub.2C.ident.CCF.sub.3 D-43 Cl Cl CH.sub.2C.ident.CCl D-44 Cl F
CH.sub.2C.ident.CCl D-45 F Cl CH.sub.2C.ident.CCl D-46 F F
CH.sub.2C.ident.CCl D-47 Cl Cl CH(CH.sub.3)C.ident.CH D-48 Cl F
CH(CH.sub.3)C.ident.CH D-49 F Cl CH(CH.sub.3)C.ident.CH D-50 F F
CH(CH.sub.3)C.ident.CH D-51 Cl Cl CH(CH.sub.3)C.ident.CCl D-52 Cl F
CH(CH.sub.3)C.ident.CCl D-53 F Cl CH(CH.sub.3)C.ident.CCl D-54 F F
CH(CH.sub.3)C.ident.CCl D-55 Cl F CH.dbd.CH--C.sub.6H.sub.5 D-56 F
Cl CH.dbd.CH--C.sub.6H.sub.5 D-57 F F CH.dbd.CH--C.sub.6H.sub.5
D-58 Cl Cl C.ident.C--C.sub.6H.sub.5 D-59 Cl F
C.ident.C--C.sub.6H.sub.5 D-60 F Cl C.ident.C--C.sub.6H.sub.5 D-61
F F C.ident.C--C.sub.6H.sub.5 D-62 Cl Cl
CH.sub.2--C.ident.C--C.sub.6H.sub.5 D-63 Cl F
CH.sub.2--C.ident.C--C.sub.6H.sub.5 D-64 F Cl
CH.sub.2--C.ident.C--C.sub.6H.sub.5 D-65 F F
CH.sub.2--C.ident.C--C.sub.6H.sub.5 D-66 Cl F CH.dbd.CHCH.sub.3
D-67 F Cl CH.dbd.CHCH.sub.3 D-68 F F CH.dbd.CHCH.sub.3 D-69 Cl F
C(CH.sub.3).dbd.CH.sub.2 D-70 F Cl C(CH.sub.3).dbd.CH.sub.2 D-71 F
F C(CH.sub.3).dbd.CH.sub.2 D-72 Cl F CH.dbd.CHCH.sub.2CH.sub.3 D-73
F Cl CH.dbd.CHCH.sub.2CH.sub.3 D-74 F F CH.dbd.CHCH.sub.2CH.sub.3
D-75 Cl F CH.sub.2CH.sub.2CH.dbd.CH.sub.2 D-76 F Cl
CH.sub.2CH.sub.2CH.dbd.CH.sub.2 D-77 F F
CH.sub.2CH.sub.2CH.dbd.CH.sub.2 D-78 Cl F CH(CH.dbd.CH.sub.2).sub.2
D-79 F Cl CH(CH.dbd.CH.sub.2).sub.2 D-80 F F
CH(CH.dbd.CH.sub.2).sub.2 D-81 Cl F CH.dbd.C(CH.sub.3).sub.2 D-82 F
Cl CH.dbd.C(CH.sub.3).sub.2 D-83 F F CH.dbd.C(CH.sub.3).sub.2 D-84
Cl F CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3 D-85 F Cl
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3 D-86 F F
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3 D-87 Cl F
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 D-88 F Cl
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 D-89 F F
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 D-90 Cl F
CH.dbd.CHC(CH.sub.3).sub.3 D-91 F Cl CH.dbd.CHC(CH.sub.3).sub.3
D-92 F F CH.dbd.CHC(CH.sub.3).sub.3 D-93 Cl F C.ident.CH D-94 F Cl
C.ident.CH D-95 F F C.ident.CH D-96 Cl F C.ident.CCH.sub.3 D-97 F
Cl C.ident.CCH.sub.3 D-98 F F C.ident.CCH.sub.3 D-99 Cl F
C.ident.CCH.sub.2CH.sub.3 D-100 F Cl C.ident.CCH.sub.2CH.sub.3
D-101 F F C.ident.CCH.sub.2CH.sub.3 D-102 Cl F
CH.sub.2CH.sub.2C.ident.CH D-103 F Cl CH.sub.2CH.sub.2C.ident.CH
D-104 F F CH.sub.2CH.sub.2C.ident.CH D-105 Cl F
CH(C.ident.CH).sub.2 D-106 F Cl CH(C.ident.CH).sub.2 D-107 F F
CH(C.ident.CH).sub.2 D-108 Cl F C.ident.CCH.sub.2CH.sub.2CH.sub.3
D-109 F Cl C.ident.CCH.sub.2CH.sub.2CH.sub.3 D-110 F F
C.ident.CCH.sub.2CH.sub.2CH.sub.3 D-111 Cl F
C.ident.CCH(CH.sub.3).sub.2 D-112 F Cl C.ident.CCH(CH.sub.3).sub.2
D-113 F F C.ident.CCH(CH.sub.3).sub.2 D-114 Cl F
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3 D-115 F Cl
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3 D-116 F F
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3 D-117 Cl F
C.ident.CC(CH.sub.3).sub.3 D-118 F Cl C.ident.CC(CH.sub.3).sub.3
D-119 F F C.ident.CC(CH.sub.3).sub.3 D-120 Cl F
CH.sub.2C.ident.CCH.sub.2CH.sub.3 D-121 F Cl
CH.sub.2C.ident.CCH.sub.2CH.sub.3 D-122 F F
CH.sub.2C.ident.CCH.sub.2CH.sub.3 D-123 Cl F
CH.dbd.CH-(4-F--C.sub.6H.sub.4) D-124 F Cl
CH.dbd.CH-(4-F--C.sub.6H.sub.4) D-125 F F
CH.dbd.CH-(4-F--C.sub.6H.sub.4) D-126 Cl F
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4) D-127 F Cl
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4) D-128 F F
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4) D-129 Cl Cl
CH.dbd.CHCH.sub.2OCH.sub.3 D-130 Cl F CH.dbd.CHCH.sub.2OCH.sub.3
D-131 F Cl CH.dbd.CHCH.sub.2OCH.sub.3 D-132 F F
CH.dbd.CHCH.sub.2OCH.sub.3 D-133 Cl Cl CH.dbd.CCl.sub.2 D-134 Cl F
CH.dbd.CCl.sub.2 D-135 F Cl CH.dbd.CCl.sub.2 D-136 F F
CH.dbd.CCl.sub.2 D-137 Cl Cl CH.dbd.CHOCH.sub.3 D-138 Cl F
CH.dbd.CHOCH.sub.3 D-139 F Cl CH.dbd.CHOCH.sub.3 D-140 F F
CH.dbd.CHOCH.sub.3 D-141 Cl Cl CH.sub.2C.ident.CCH(CH.sub.3).sub.2
D-142 Cl F CH.sub.2C.ident.CCH(CH.sub.3).sub.2 D-143 F Cl
CH.sub.2C.ident.CCH(CH.sub.3).sub.2 D-144 F F
CH.sub.2C.ident.CCH(CH.sub.3).sub.2 D-145 Cl Cl
CH.sub.2C.ident.CC(CH.sub.3).sub.3 D-146 Cl F
CH.sub.2C.ident.CC(CH.sub.3).sub.3 D-147 F Cl
CH.sub.2C.ident.CC(CH.sub.3).sub.3 D-148 F F
CH.sub.2C.ident.CC(CH.sub.3).sub.3 D-149 Cl Cl
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 D-150 Cl F
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 D-151 F Cl
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 D-152 F F
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 D-153 Cl Cl
CH.sub.2C(Cl).dbd.CHCl D-154 Cl F CH.sub.2C(Cl).dbd.CHCl D-155 F Cl
CH.sub.2C(Cl).dbd.CHCl D-156 F F CH.sub.2C(Cl).dbd.CHCl
[0069] A further embodiment of the present invention are novel
compounds of formula XII:
##STR00020##
[0070] Wherein the variables X.sup.1, X.sup.2, R.sup.1 and R.sup.2
are as defined and preferably defined for formula I herein. In
specific embodiments of compounds XII according to the present
invention, the substituents X.sup.1, X.sup.2, R.sup.1 and R.sup.2
are as defined in tables 1 to 148 and 148a to 148z and 148aa to
148jj and 149 to 296 and 296a to 296z and 296aa to 296jj, wherein
the substituents are specific embodiments independently of each
other or in any combination.
[0071] A further embodiment of the present invention are novel
compounds of formula XIII:
##STR00021##
[0072] Wherein the variables X.sup.1, X.sup.2, R.sup.1 and R.sup.2
are as defined and preferably defined for formula I herein, wherein
LG stands for a leaving group as defined above. In specific
embodiments of compounds XIII according to the present invention,
the substituents X.sup.1, X.sup.2, R.sup.1 and R.sup.2 are as
defined in tables 1 to 148 and 148a to 148z and 148aa to 148jj and
149 to 296 and 296a to 296z and 296aa to 296jj, wherein the
substituents are specific embodiments independently of each other
or in any combination.
[0073] In the definitions of the variables given herein, collective
terms are used which are generally representative for the
substituents in question. The term "C.sub.n-C.sub.m" indicates the
number of carbon atoms possible in each case in the substituent or
substituent moiety in question.
[0074] The term "halogen" refers to fluorine, chlorine, bromine and
iodine.
[0075] The term "C.sub.1-C.sub.6-alkyl" refers to a
straight-chained or branched saturated hydrocarbon group having 1
to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1-methylethyl,
butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,
1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,
1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl,
1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,
1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,
1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,
1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and
1-ethyl-2-methylpropyl. Likewise, the term "C.sub.2-C.sub.4-alkyl"
refers to a straight-chained or branched alkyl group having 2 to 4
carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl
(iso-propoyl), butyl, 1-methylpropyl (sec.-butyl), 2-methylpropyl
(iso-butyl), 1,1-dimethylethyl (tert.-butyl).
[0076] The term "C.sub.2-C.sub.4-alkenyl" refers to a
straight-chain or branched unsaturated hydrocarbon radical having 2
to 4 carbon atoms and a double bond in any position, e.g. ethenyl,
1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl,
2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,
1-methyl-2-propenyl, 2-methyl-2-propenyl. Likewise, the term
"C.sub.2-C.sub.6-alkenyl" refers to a straight-chain or branched
unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a
double bond in any position.
[0077] The term "C.sub.2-C.sub.4-alkynyl" refers to a
straight-chain or branched unsaturated hydrocarbon radical having 2
to 4 carbon atoms and containing at least one triple bond, such as
ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl,
but-2-ynyl, but-3-ynyl, 1-methyl-prop-2-ynyl. Likewise, the term
"C.sub.2-C.sub.6-alkynyl" refers to a straight-chain or branched
unsaturated hydrocarbon radical having 2 to 6 carbon atoms and at
least one triple bond.
[0078] The term "C.sub.1-C.sub.4-halogenalkyl" refers to a
straight-chained or branched alkyl group having 1 to 4 carbon
atoms, wherein some or all of the hydrogen atoms in these groups
may be replaced by halogen atoms as mentioned above, for example
chloromethyl, bromomethyl, dichloromethyl, trichloromethyl,
fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,
dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl,
1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,
2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,
2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,
2,2,2-trichloroethyl and pentafluoroethyl, 2-fluoropropyl,
3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,
2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,
3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,
CH.sub.2--C.sub.2F.sub.5, CF.sub.2--C.sub.2F.sub.5,
CF(CF.sub.3).sub.2, 1-fluoromethyl-2-fluoroethyl,
1-(chloromethyl)-2-chloroethyl, 1-bromomethyl-2-bromoethyl,
4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, and
the like.
[0079] The term "C.sub.3-C.sub.8-cycloalkyl" refers to monocyclic
saturated hydrocarbon radicals having 3 to 8 carbon ring members,
such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
cycloheptyl or cyclooctyl.
[0080] The term "C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl"
refers to alkyl having 1 to 4 carbon atoms (as defined above),
wherein one hydrogen atom of the alkyl radical is replaced by a
cycloalkyl radical having 3 to 8 carbon atoms (as defined
above).
[0081] The term "C.sub.1-C.sub.4-alkoxy" refers to a straight-chain
or branched alkyl group having 1 to 4 carbon atoms which is bonded
via an oxygen, at any position in the alkyl group, e.g. methoxy,
ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,
2-methylpropoxy or 1,1-dimethylethoxy.
[0082] The term "C.sub.1-C.sub.4-halogenalkoxy" refers to a
C.sub.1-C.sub.4-alkoxy radical as defined above, wherein some or
all of the hydrogen atoms in these groups may be replaced by
halogen atoms as mentioned above, e.g., OCH.sub.2F, OCHF.sub.2,
OCF.sub.3, OCH.sub.2Cl, OCHCl.sub.2, OCCl.sub.3,
chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy,
2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy,
2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,
2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
2,2,2-trichloroethoxy, OC.sub.2F.sub.5, 2-fluoropropoxy,
3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2
chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy,
2-bromopropoxy, 3 bromopropoxy, 3,3,3-trifluoropropoxy,
3,3,3-trichloropropoxy, OCH.sub.2--C.sub.2F.sub.5,
OCF.sub.2--C.sub.2F.sub.5, 1-fluoromethyl-2-fluoroethoxy,
1-chloromethyl-2-chloroethoxy, 1-bromomethyl-2-bromoethoxy,
4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or
nonafluorobutoxy.
[0083] Agriculturally acceptable salts of compounds I encompass
especially the salts of those cations or the acid addition salts of
those acids whose cations and anions, respectively, have no adverse
effect on the fungicidal action of the compounds I. Suitable
cations are thus in particular the ions of the alkali metals,
preferably sodium and potassium, of the alkaline earth metals,
preferably calcium, magnesium and barium, of the transition metals,
preferably manganese, copper, zinc and iron, and also the ammonium
ion which, if desired, may carry one to four C.sub.1-C.sub.4-alkyl
substituents and/or one phenyl or benzyl substituent, preferably
diisopropylammonium, tetramethylammonium, tetrabutylammonium,
trimethylbenzylammonium, furthermore phosphonium ions, sulfonium
ions, preferably tri(C.sub.1-C.sub.4-alkyl)sulfonium, and
sulfoxonium ions, preferably tri(C.sub.1-C.sub.4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride,
bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,
hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate,
hexafluorosilicate, hexafluorophosphate, benzoate, and the anions
of C.sub.1-C.sub.4-alkanoic acids, preferably formate, acetate,
propionate and butyrate. They can be formed by reacting a compound
of formula I with an acid of the corresponding anion, preferably of
hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid
or nitric acid.
[0084] The compounds of formula I can be present in atropisomers
arising from restricted rotation about a single bond of asymmetric
groups. They also form part of the subject matter of the present
invention.
[0085] Depending on the substitution pattern, the compounds of
formula I and their N-oxides may have one or more centers of
chirality, in which case they are present as pure enantiomers or
pure diastereomers or as enantiomer or diastereomer mixtures. Both,
the pure enantiomers or diastereomers and their mixtures are
subject matter of the present invention.
[0086] In respect of the variables, the embodiments of the
intermediates correspond to the embodiments of the compounds I.
[0087] Preference is given to those compounds I and where
applicable also to compounds of all sub-formulae such as I.A
provided herein and to the intermediates such as compounds VIII,
XI, XII and XIII, wherein the substituents (such as X.sup.1,
X.sup.2, R.sup.1, R.sup.2, R.sup.a and R.sup.b) have independently
of each other or more preferably in combination the following
meanings: [0088] According to the invention, X.sup.1 and X.sup.2
are independently selected from halogen. [0089] One embodiment
relates to compounds I, wherein X.sup.1 is F or Cl, in particular
Cl. [0090] Another embodiment relates to compounds I, wherein
X.sup.2 is F or Cl, in particular Cl. According to the invention,
R.sup.1 is C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl.
R.sup.1 is unsubstituted or may carry 1, 2, 3 or up to the maximum
possible number of identical or different groups R.sup.a, which
independently of one another are selected from halogen, CN, nitro,
phenyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-halogenalkoxy,
wherein the phenyl is unsubstituted or may carry 1, 2, 3, 4 or 5
substituents selected from halogen, CN, nitro,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkyl and
C.sub.1-C.sub.4-halogenalkoxy.
[0091] According to one embodiment, R.sup.1 is
C.sub.2-C.sub.6-alkenyl, wherein one specific embodiment thereof
relates to compounds, wherein the alkenyl is unsubstituted and
another embodiment relates to compounds, wherein the alkenyl is
substituted by 1, 2 or 3 R.sup.a, independently selected from
halogen, CN, nitro, C.sub.1-C.sub.2-alkoxy and
C.sub.1-C.sub.2-halogenalkoxy.
[0092] A further embodiment relates to compounds I, wherein R.sup.1
is C.sub.2-C.sub.6-alkenyl, more preferably
C.sub.2-C.sub.4-alkenyl, in particular selected from allyl and
methylallyl, wherein the aforementioned groups may be substituted
by R.sup.a as defined above, more preferably they may carry 1, 2 or
3 halogen substituents, in particular selected from Cl and F.
According to one embodiment, R.sup.1 is
CH.sub.2--C(CH.sub.3).dbd.CH.sub.2, according to another
embodiment, R.sup.1 is CH.sub.2--CH.dbd.CH--CH.sub.3, wherein in
these embodiments, the R.sup.1 may carry 1, 2 or 3 R.sup.a as
defined above, in particular, they may carry 1, 2 or 3 halogen
substituents, in particular selected from Cl and F.
[0093] According to a further embodiment, R.sup.1 is
C.sub.2-C.sub.6-alkynyl. Specific embodiments are prop-1-ynyl,
ethynyl, prop-2-ynyl and but-2-ynyl. According to one specific
embodiment thereof relates to compounds, wherein the alkynyl is
unsubstituted and another embodiment, relates to compounds, wherein
the alkynyl is substituted by 1, 2 or 3 R.sup.a, independently
selected from halogen, CN, nitro, C.sub.1-C.sub.2-alkoxy and
C.sub.1-C.sub.2-halogenalkoxy.
[0094] A further embodiment relates to compounds I, wherein R.sup.1
is C.sub.2-C.sub.6-alkynyl, more preferably
C.sub.2-C.sub.6-alk-1-ynyl, in particular selected from ethynyl,
prop-1-ynyl, but-1-ynyl and 3-dimethyl-but-1-ynyl, wherein the
aforementioned groups may be substituted by R.sup.a as defined
above, more preferably they may carry 1, 2 or 3 halogen
substituents, in particular selected from Cl and F.
[0095] A further embodiment relates to compounds I, wherein R.sup.1
is C.sub.2-C.sub.4-alkynyl, more preferably propargyl, wherein the
aforementioned groups may be substituted by R.sup.a as defined
above. According to a further specific embodiment, R.sup.1 is
ethynyl.
[0096] A further embodiment relates to compounds I, wherein R.sup.1
is unsubstituted.
[0097] According to a further embodiment, R.sup.1 carries 1, 2 or 3
R.sup.a, independently selected from F, Cl, CN,
C.sub.1-C.sub.2-alkoxy and C.sub.1-C.sub.2-halogenalkoxy.
[0098] A further embodiment relates to compounds I, wherein R.sup.1
carries one phenyl R.sup.a group, more preferably R.sup.1 is
phenylethenyl or phenylethynyl, wherein aforementioned phenyl
moieties may be substituted by 1, 2 or 3 halogen substituents, in
particular selected from Cl and F.
[0099] According to the invention, R.sup.2 is
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, phenyl,
phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.2-C.sub.4-alkenyl or
phenyl-C.sub.2-C.sub.4-alkynyl; wherein the aliphatic moieties are
unsubstituted or carry 1, 2, 3 or up to the maximum possible number
of identical or different groups R.sup.a which independently of one
another are selected from halogen, CN, nitro, phenyl,
C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-halogenalkoxy, wherein
the phenyl may be substituted by 1, 2, 3, 4, or 5 substituents
selected from halogen, CN, nitro, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkyl and
C.sub.1-C.sub.4-halogenalkoxy; and wherein the cycloalkyl and/or
phenyl moieties of R.sup.2 may carry 1, 2, 3, 4, 5 or up to the
maximum number of identical or different groups R.sup.b which
independently of one another are selected from halogen, CN, nitro,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy,
C.sub.1-C.sub.4-halogenalkyl and C.sub.1-C.sub.4-halogenalkoxy.
[0100] According to one embodiment, R.sup.2 is
C.sub.1-C.sub.6-alkyl, in particular C.sub.1-C.sub.4-alkyl.
Specific embodiments relate to compounds, wherein R.sup.2 is
methyl, ethyl or isopropyl. According to one embodiment, the alkyl
is unsubstituted, according to another embodiment, the alkyl
carries 1, 2, 3, 4, 5 or 6, in particular 1, 2, 3 or 4, R.sup.a,
wherein R.sup.a is selected from F, Cl, Br, CN,
C.sub.1-C.sub.2-alkoxy and C.sub.1-C.sub.2-halogenalkoxy.
[0101] According to a further embodiment, R.sup.2 is
C.sub.2-C.sub.6-alkenyl, in particular C.sub.2-C.sub.4-alkenyl.
Specific embodiments relate to compounds, wherein R.sup.2 is allyl.
According to one embodiment, the alkenyl is unsubstituted,
according to another embodiment, the alkenyl carries 1, 2, 3, 4, 5
or 6, in particular 1, 2, 3 or 4, R.sup.a, wherein R.sup.a is
selected from F, Cl, Br, CN, C.sub.1-C.sub.2-alkoxy and
C.sub.1-C.sub.2-halogenalkoxy.
[0102] According to a further embodiment, R.sup.2 is
C.sub.2-C.sub.6-alkynyl, in particular C.sub.2-C.sub.4-alkynyl.
Specific embodiments relate to compounds, wherein R.sup.2 is
propargyl. According to one embodiment, the alkynyl is
unsubstituted, according to another embodiment, the alkynyl carries
1, 2, 3, 4, 5 or 6, in particular 1, 2, 3 or 4, R.sup.a, wherein
R.sup.a is selected from F, Cl, Br, CN, C.sub.1-C.sub.2-alkoxy and
C.sub.1-C.sub.2-halogenalkoxy.
[0103] A further embodiment relates to compounds I, wherein R.sup.2
is C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl,
C.sub.2-C.sub.4-alkynyl, cyclopropyl, cyclopropylmethyl, phenyl,
benzyl, phenylethenyl or phenylethynyl, wherein the aforementioned
groups may be substituted by R.sup.a and/or Rb as defined above,
more preferably they carry 1, 2 or 3 halogen substituents, even
more preferably R.sup.2 is C.sub.1-C.sub.2-haloalkyl, in particular
R.sup.2 is CF.sub.3.
[0104] A further embodiment relates to compounds I, wherein R.sup.2
is C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl,
C.sub.2-C.sub.4-alkynyl, cyclopropyl, cyclopropylmethyl, phenyl,
benzyl, phenylethenyl or phenylethynyl, more preferably from
C.sub.1-C.sub.4-alkyl, in particular methyl.
[0105] According to a further embodiment, R.sup.2 is
C.sub.3-C.sub.8-cycloalkyl, in particular
C.sub.3-C.sub.6-cycloalkyl. Specific embodiments relate to
compounds, wherein R.sup.2 is cyclopropyl. According to one
embodiment, the cycloalkyl is unsubstituted, according to another
embodiment, the cycloalkyl carries 1, 2, 3, 4, 5 or 6, in
particular 1, 2, 3 or 4, Rb, wherein R.sup.b is selected from F,
Cl, Br, CN, C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.2-alkoxy,
C.sub.1-C.sub.2-halogenalkyl and C.sub.1-C.sub.2-halogenalkoxy.
[0106] According to a further embodiment, R.sup.2 is
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, in particular
C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl. Specific
embodiments relate to compounds, wherein R.sup.2 is
cyclopropylmethyl. According to one embodiment, the cycloalkyl
moiety is unsubstituted, according to another embodiment, the
cycloalkyl moiety carries 1, 2, 3, 4, 5 or 6, in particular 1, 2, 3
or 4, Rb, wherein R.sup.b is selected from F, Cl, Br, CN,
C.sub.1-C.sub.2-alkyl, C.sub.1-C.sub.2-alkoxy,
C.sub.1-C.sub.2-halogenalkyl and C.sub.1-C.sub.2-halogenalkoxy.
According to a further embodiment, the alkyl moiety is
unsubstituted, according to another embodiment, the alkyl moiety
carries 1, 2, 3, 4, 5 or 6, in particular 1, 2, 3 or 4, R.sup.a,
wherein R.sup.a is selected from F, Cl, Br, CN,
C.sub.1-C.sub.2-alkoxy and C.sub.1-C.sub.2-halogenalkoxy.
[0107] A further embodiment relates to compounds I, wherein R.sup.2
is C.sub.3-C.sub.8-cycloalkyl or
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, more preferably
selected from cyclopropyl and cyclopropylmethyl, wherein the
aforementioned groups may be substituted by R.sup.a and/or Rb as
defined above.
[0108] A further embodiment relates to compounds I, wherein R.sup.2
is unsubstituted.
[0109] A further embodiment relates to compounds, wherein X.sup.1
and X.sup.2 are both Cl and R.sup.1 is ethynyl, which compounds are
of formula I.B:
##STR00022##
[0110] A further embodiment relates to compounds, wherein X.sup.1
and X.sup.2 are both Cl and R.sup.1 is C.ident.CCH.sub.3, which
compounds are of formula I.C:
##STR00023##
[0111] A further embodiment relates to compounds, wherein X.sup.1
and X.sup.2 are both Cl and R.sup.1 is CH.sub.2C.ident.CH, which
compounds are of formula I.D:
##STR00024##
[0112] Particularly preferred embodiments of the invention relate
to compounds I, wherein the combination of X.sup.1, X.sup.2 and
R.sup.1 (including R.sup.a, R.sup.b) is as defined in Table P
below.
TABLE-US-00003 TABLE P line X.sup.1 X.sup.2 R.sup.1 P-1 Cl Cl
--CH.dbd.CH.sub.2 P-2 Cl F --CH.dbd.CH.sub.2 P-3 F Cl
--CH.dbd.CH.sub.2 P-4 F F --CH.dbd.CH.sub.2 P-5 Cl Cl
--CH.sub.2CH.dbd.CH.sub.2 P-6 Cl F --CH.sub.2CH.dbd.CH.sub.2 P-7 F
Cl --CH.sub.2CH.dbd.CH.sub.2 P-8 F F --CH.sub.2CH.dbd.CH.sub.2 P-9
Cl Cl --CH.sub.2CH.dbd.CHCH.sub.3 P-10 Cl F
--CH.sub.2CH.dbd.CHCH.sub.3 P-11 F Cl --CH.sub.2CH.dbd.CHCH.sub.3
P-12 F F --CH.sub.2CH.dbd.CHCH.sub.3 P-13 Cl Cl
--CH.sub.2CH.dbd.CHF P-14 Cl F --CH.sub.2CH.dbd.CHF P-15 F Cl
--CH.sub.2CH.dbd.CHF P-16 F F --CH.sub.2CH.dbd.CHF P-17 Cl Cl
--CH.sub.2CH.dbd.CHCl P-18 Cl F --CH.sub.2CH.dbd.CHCl P-19 F Cl
--CH.sub.2CH.dbd.CHCl P-20 F F --CH.sub.2CH.dbd.CHCl P-21 Cl Cl
--CH.sub.2C(CH.sub.3).dbd.CH.sub.2 P-22 Cl F
--CH.sub.2C(CH.sub.3).dbd.CH.sub.2 P-23 F Cl
--CH.sub.2C(CH.sub.3).dbd.CH.sub.2 P-24 F F
--CH.sub.2C(CH.sub.3).dbd.CH.sub.2 P-25 Cl Cl
--CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 P-26 Cl F
--CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 P-27 F Cl
--CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 P-28 F F
--CH.sub.2C(CH.sub.3).dbd.CHCH.sub.3 P-29 Cl Cl
--CH.sub.2C(CH.sub.3).dbd.CHF P-30 Cl F
--CH.sub.2C(CH.sub.3).dbd.CHF P-31 F Cl
--CH.sub.2C(CH.sub.3).dbd.CHF P-32 F F
--CH.sub.2C(CH.sub.3).dbd.CHF P-33 Cl Cl
--CH.sub.2C(CH.sub.3).dbd.CHCl P-34 Cl F
--CH.sub.2C(CH.sub.3).dbd.CHCl P-35 F Cl
--CH.sub.2C(CH.sub.3).dbd.CHCl P-36 F F
--CH.sub.2C(CH.sub.3).dbd.CHCl P-37 Cl Cl --CH.sub.2C.ident.CH P-38
Cl F --CH.sub.2C.ident.CH P-39 F Cl --CH.sub.2C.ident.CH P-40 F F
--CH.sub.2C.ident.CH P-41 Cl Cl --CH.sub.2C.ident.CCH.sub.3 P-42 Cl
F --CH.sub.2C.ident.CCH.sub.3 P-43 F Cl --CH.sub.2C.ident.CCH.sub.3
P-44 F F --CH.sub.2C.ident.CCH.sub.3 P-45 Cl Cl
--CH.sub.2C.ident.CCF.sub.3 P-46 Cl F --CH.sub.2C.ident.CCF.sub.3
P-47 F Cl --CH.sub.2C.ident.CCF.sub.3 P-48 F F
--CH.sub.2C.ident.CCF.sub.3 P-49 Cl Cl --CH.sub.2C.ident.CCl P-50
Cl F --CH.sub.2C.ident.CCl P-51 F Cl --CH.sub.2C.ident.CCl P-52 F F
--CH.sub.2C.ident.CCl P-53 Cl Cl --CH(CH.sub.3)C.ident.CH P-54 Cl F
--CH(CH.sub.3)C.ident.CH P-55 F Cl --CH(CH.sub.3)C.ident.CH P-56 F
F --CH(CH.sub.3)C.ident.CH P-57 Cl Cl --CH(CH.sub.3)C.ident.CCl
P-58 Cl F --CH(CH.sub.3)C.ident.CCl P-59 F Cl
--CH(CH.sub.3)C.ident.CCl P-60 F F --CH(CH.sub.3)C.ident.CCl P-61
Cl Cl --CH.dbd.CH--C.sub.6H.sub.5 P-62 Cl F
--CH.dbd.CH--C.sub.6H.sub.5 P-63 F Cl --CH.dbd.CH--C.sub.6H.sub.5
P-64 F F --CH.dbd.CH--C.sub.6H.sub.5 P-65 Cl Cl
--C.ident.C--C.sub.6H.sub.5 P-66 Cl F --C.ident.C--C.sub.6H.sub.5
P-67 F Cl --C.ident.C--C.sub.6H.sub.5 P-68 F F
--C.ident.C--C.sub.6H.sub.5 P-69 Cl Cl
--CH.sub.2--C.ident.C--C.sub.6H.sub.5 P-70 Cl F
--CH.sub.2--C.ident.C--C.sub.6H.sub.5 P-71 F Cl
--CH.sub.2--C.ident.C--C.sub.6H.sub.5 P-72 F F
--CH.sub.2--C.ident.C--C.sub.6H.sub.5 P-73 Cl Cl CH.dbd.CHCH.sub.3
P-74 Cl F CH.dbd.CHCH.sub.3 P-75 F Cl CH.dbd.CHCH.sub.3 P-76 F F
CH.dbd.CHCH.sub.3 P-77 Cl Cl C(CH.sub.3).dbd.CH.sub.2 P-78 Cl F
C(CH.sub.3).dbd.CH.sub.2 P-79 F Cl C(CH.sub.3).dbd.CH.sub.2 P-80 F
F C(CH.sub.3).dbd.CH.sub.2 P-81 Cl Cl CH.dbd.CHCH.sub.2CH.sub.3
P-82 Cl F CH.dbd.CHCH.sub.2CH.sub.3 P-83 F Cl
CH.dbd.CHCH.sub.2CH.sub.3 P-84 F F CH.dbd.CHCH.sub.2CH.sub.3 P-85
Cl Cl CH.sub.2CH.sub.2CH.dbd.CH.sub.2 P-86 Cl F
CH.sub.2CH.sub.2CH.dbd.CH.sub.2 P-87 F Cl
CH.sub.2CH.sub.2CH.dbd.CH.sub.2 P-88 F F
CH.sub.2CH.sub.2CH.dbd.CH.sub.2 P-89 Cl Cl
CH(CH.dbd.CH.sub.2).sub.2 P-90 Cl F CH(CH.dbd.CH.sub.2).sub.2 P-91
F Cl CH(CH.dbd.CH.sub.2).sub.2 P-92 F F CH(CH.dbd.CH.sub.2).sub.2
P-93 Cl Cl CH.dbd.C(CH.sub.3).sub.2 P-94 Cl F
CH.dbd.C(CH.sub.3).sub.2 P-95 F Cl CH.dbd.C(CH.sub.3).sub.2 P-96 F
F CH.dbd.C(CH.sub.3).sub.2 P-97 Cl Cl
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3 P-98 Cl F
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3 P-99 F Cl
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3 P-100 F F
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.3 P-101 Cl Cl
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 P-102 Cl F
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 P-103 F Cl
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 P-104 F F
CH.dbd.CHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 P-105 Cl Cl
CH.dbd.CHC(CH.sub.3).sub.3 P-106 Cl F CH.dbd.CHC(CH.sub.3).sub.3
P-107 F Cl CH.dbd.CHC(CH.sub.3).sub.3 P-108 F F
CH.dbd.CHC(CH.sub.3).sub.3 P-109 Cl Cl C.ident.CH P-110 Cl F
C.ident.CH P-111 F Cl C.ident.CH P-112 F F C.ident.CH P-113 Cl Cl
C.ident.CCH.sub.3 P-114 Cl F C.ident.CCH.sub.3 P-115 F Cl
C.ident.CCH.sub.3 P-116 F F C.ident.CCH.sub.3 P-117 Cl Cl
C.ident.CCH.sub.2CH.sub.3 P-118 Cl F C.ident.CCH.sub.2CH.sub.3
P-119 F Cl C.ident.CCH.sub.2CH.sub.3 P-120 F F
C.ident.CCH.sub.2CH.sub.3 P-121 Cl Cl CH.sub.2CH.sub.2C.ident.CH
P-122 Cl F CH.sub.2CH.sub.2C.ident.CH P-123 F Cl
CH.sub.2CH.sub.2C.ident.CH P-124 F F CH.sub.2CH.sub.2C.ident.CH
P-125 Cl Cl CH(C.ident.CH).sub.2 P-126 Cl F CH(C.ident.CH).sub.2
P-127 F Cl CH(C.ident.CH).sub.2 P-128 F F CH(C.ident.CH).sub.2
P-129 Cl Cl C.ident.CCH.sub.2CH.sub.2CH.sub.3 P-130 Cl F
C.ident.CCH.sub.2CH.sub.2CH.sub.3 P-131 F Cl
C.ident.CCH.sub.2CH.sub.2CH.sub.3 P-132 F F
C.ident.CCH.sub.2CH.sub.2CH.sub.3 P-133 Cl Cl
C.ident.CCH(CH.sub.3).sub.2 P-134 Cl F C.ident.CCH(CH.sub.3).sub.2
P-135 F Cl C.ident.CCH(CH.sub.3).sub.2 P-136 F F
C.ident.CCH(CH.sub.3).sub.2 P-137 Cl Cl
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3 P-138 Cl F
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3 P-139 F Cl
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3 P-140 F F
C.ident.CCH.sub.2CH.sub.2CH.sub.2CH.sub.3 P-141 Cl Cl
C.ident.CC(CH.sub.3).sub.3 P-142 Cl F C.ident.CC(CH.sub.3).sub.3
P-143 F Cl C.ident.CC(CH.sub.3).sub.3 P-144 F F
C.ident.CC(CH.sub.3).sub.3 P-145 Cl Cl
CH.sub.2C.ident.CCH.sub.2CH.sub.3 P-146 Cl F
CH.sub.2C.ident.CCH.sub.2CH.sub.3 P-147 F Cl
CH.sub.2C.ident.CCH.sub.2CH.sub.3 P-148 F F
CH.sub.2C.ident.CCH.sub.2CH.sub.3 P-149 Cl Cl
CH.dbd.CH-(4-F--C.sub.6H.sub.4) P-150 Cl F
CH.dbd.CH-(4-F--C.sub.6H.sub.4) P-151 F Cl
CH.dbd.CH-(4-F--C.sub.6H.sub.4) P-152 F F
CH.dbd.CH-(4-F--C.sub.6H.sub.4) P-153 Cl Cl
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4) P-154 Cl F
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4) P-155 F Cl
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4) P-156 F F
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4) P-157 Cl Cl
CH.dbd.CHCH.sub.2OCH.sub.3 P-158 Cl F CH.dbd.CHCH.sub.2OCH.sub.3
P-159 F Cl CH.dbd.CHCH.sub.2OCH.sub.3 P-160 F F
CH.dbd.CHCH.sub.2OCH.sub.3 P-161 Cl Cl CH.dbd.CCl.sub.2 P-162 Cl F
CH.dbd.CCl.sub.2 P-163 F Cl CH.dbd.CCl.sub.2 P-164 F F
CH.dbd.CCl.sub.2 P-165 Cl Cl CH.dbd.CHOCH.sub.3 P-166 Cl F
CH.dbd.CHOCH.sub.3 P-167 F Cl CH.dbd.CHOCH.sub.3 P-168 F F
CH.dbd.CHOCH.sub.3 P-169 Cl Cl CH.sub.2C.ident.CCH(CH.sub.3).sub.2
P-170 Cl F CH.sub.2C.ident.CCH(CH.sub.3).sub.2 P-171 F Cl
CH.sub.2C.ident.CCH(CH.sub.3).sub.2 P-172 F F
CH.sub.2C.ident.CCH(CH.sub.3).sub.2 P-173 Cl Cl
CH.sub.2C.ident.CC(CH.sub.3).sub.3 P-174 Cl F
CH.sub.2C.ident.CC(CH.sub.3).sub.3 P-175 F Cl
CH.sub.2C.ident.CC(CH.sub.3).sub.3 P-176 F F
CH.sub.2C.ident.CC(CH.sub.3).sub.3 P-177 Cl Cl
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 P-178 Cl F
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 P-179 F Cl
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 P-180 F F
CH.sub.2C.ident.CCH.sub.2OCH.sub.3 P-181 Cl Cl
CH.sub.2C(Cl).dbd.CHCl P-182 Cl F CH.sub.2C(Cl).dbd.CHCl P-183 F Cl
CH.sub.2C(Cl).dbd.CHCl P-184 F F CH.sub.2C(Cl).dbd.CHCl
[0113] A skilled person will readily understand that the
preferences given in connection with compounds I apply for formula
VIII, XI and XII etc. as defined above.
[0114] With respect to their use, particular preference is given to
compounds 1 to 5520 and 1a to 5520a of formula I compiled in Tables
1 to 148 and 148a to 148z and 148aa to 148jj and 149 to 296 and
296a to 296z and 296aa to 296jj below. The groups mentioned in the
Tables for a substituent are furthermore, independently of the
combination wherein they are mentioned, a particularly preferred
embodiment of the substituent in question.
Table 1: Compounds 1 to 30 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-1 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 2: Compounds 31 to 60 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-2 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 3: Compounds
61 to 90 of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-3 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A. Table 4: Compounds 91 to 120 of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-4 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A. Table 5: Compounds 121 to 150
of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as
in line P-5 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 6: Compounds 151 to 180 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-6 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 7: Compounds 181 to 210 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-7 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table 8:
Compounds 211 to 240 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-8 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 9: Compounds 241 to 270 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-9 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 10:
Compounds 271 to 300 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-10 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 11: Compounds 301 to 330 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-11 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 12:
Compounds 331 to 360 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-12 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 13: Compounds 361 to 390 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-13 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 14:
Compounds 391 to 420 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-14 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 15: Compounds 421 to 450 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-15 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 16:
Compounds 451 to 480 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-16 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 17: Compounds 481 to 510 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-17 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 18:
Compounds 511 to 540 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-18 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 19: Compounds 541 to 570 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-19 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 20:
Compounds 571 to 600 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-20 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 21: Compounds 601 to 630 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-21 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 22:
Compounds 631 to 660 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-22 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 23: Compounds 661 to 690 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-23 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 24:
Compounds 691 to 720 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-24 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 25: Compounds 721 to 750 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-25 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 26:
Compounds 751 to 780 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-26 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 27: Compounds 781 to 810 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-27 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 28:
Compounds 811 to 840 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-28 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 29: Compounds 841 to 870 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-29 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 30:
Compounds 871 to 900 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-30 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 31: Compounds 901 to 930 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-31 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 32:
Compounds 931 to 960 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-32 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 33: Compounds 961 to 990 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-33 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 34:
Compounds 991 to 1020 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-34 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 35: Compounds 1021 to 1050 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-35 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 36:
Compounds 1051 to 1080 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-36 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 37: Compounds 1081 to 1110 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-37 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 38:
Compounds 1111 to 1140 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-38 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 39: Compounds 1141 to 1170 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-39 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 40:
Compounds 1171 to 1200 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-40 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 41: Compounds 1201 to 1230 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-41 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 42:
Compounds 1231 to 1260 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-42 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 43: Compounds 1261 to 1290 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-43 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 44:
Compounds 1291 to 1320 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-44 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 45: Compounds 1321 to 1350 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-45 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 46:
Compounds 1351 to 1380 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-46 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 47: Compounds 1381 to 1410 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-47 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 48:
Compounds 1411 to 1440 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-48 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 49: Compounds 1441 to 1470 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-49 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 50:
Compounds 1471 to 1500 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-50 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 51: Compounds 1501 to 1530 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-51 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 52:
Compounds 1531 to 1560 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-52 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 53: Compounds 1561 to 1590 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-53 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 54:
Compounds 1591 to 1620 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-54 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 55: Compounds 1621 to 1650 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-55 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 56:
Compounds 1651 to 1680 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-56 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 57: Compounds 1681 to 1710 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-57 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 58:
Compounds 1711 to 1740 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-58 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 59: Compounds 1741 to 1770 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-59 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 60:
Compounds 1771 to 1800 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-60 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 61: Compounds 1801 to 1830 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-61 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 62:
Compounds 1831 to 1860 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-62 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 63: Compounds 1861 to 1890 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-63 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 64:
Compounds 1891 to 1920 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-64 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 65: Compounds 1921 to 1950 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-65 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 66:
Compounds 1951 to 1980 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-66 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 67: Compounds 1981 to 2010 of formula I,
wherein X
.sup.1, X.sup.2 and R.sup.1 are defined as in line P-67 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A. Table 68: Compounds 2011 to
2040 of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-68 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 69: Compounds 2041 to 2070 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-69 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 70: Compounds 2071 to 2100 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-70 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table 71:
Compounds 2101 to 2130 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-71 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 72: Compounds 2131 to 2160 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-72 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 73:
Compounds 2161 to 2190 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-73 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 74: Compounds 2191 to 2220 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-74 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 75:
Compounds 2221 to 2250 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-75 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 76: Compounds 2251 to 2280 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-76 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 77:
Compounds 2281 to 2310 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-77 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 78: Compounds 2311 to 2340 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-78 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 79:
Compounds 2341 to 2370 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-79 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 80: Compounds 2371 to 2400 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-80 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 81:
Compounds 2401 to 2430 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-81 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 82: Compounds 2431 to 2460 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-82 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 83:
Compounds 2461 to 2490 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-83 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 84: Compounds 2491 to 2520 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-84 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 85:
Compounds 2521 to 2550 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-85 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 86: Compounds 2551 to 2580 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-86 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 87:
Compounds 2581 to 2610 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-87 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 88: Compounds 2611 to 2640 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-88 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 89:
Compounds 2641 to 2670 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-89 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 90: Compounds 2671 to 2700 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-90 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 91:
Compounds 2701 to 2730 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-91 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 92: Compounds 2731 to 2760 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-92 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 93:
Compounds 2761 to 2790 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-93 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 94: Compounds 2791 to 2820 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-94 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 95:
Compounds 2821 to 2850 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-95 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 96: Compounds 2851 to 2880 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-96 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 97:
Compounds 2881 to 2910 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-97 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 98: Compounds 2911 to 2940 of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-98 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 99:
Compounds 2941 to 2970 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-99 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 100: Compounds 2971 to 3000 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-100 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
101: Compounds 3001 to 3030 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-101 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 102: Compounds 3031 to 3060 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-102 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
103: Compounds 3061 to 3090 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-103 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 104: Compounds 3091 to 3120 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-104 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
105: Compounds 3121 to 3150 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-105 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 106: Compounds 3151 to 3180 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-106 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
107: Compounds 3181 to 3210 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-107 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 108: Compounds 3211 to 3240 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-108 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
109: Compounds 3241 to 3270 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-109 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 110: Compounds 3271 to 3300 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-110 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
111: Compounds 3301 to 3330 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-111 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 112: Compounds 3331 to 3360 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-112 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
113: Compounds 3361 to 3390 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-113 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 114: Compounds 3391 to 3420 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-114 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
115: Compounds 3421 to 3450 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-115 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 116: Compounds 3451 to 3480 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-116 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
117: Compounds 3481 to 3510 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-117 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 118: Compounds 3510 to 3540 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-118 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
119: Compounds 3541 to 3570 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-119 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 120: Compounds 3571 to 3600 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-120 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
121: Compounds 3601 to 3630 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-121 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 122: Compounds 3631 to 3660 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-122 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
123: Compounds 3661 to 3690 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-123 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 124: Compounds 3691 to 3720 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-124 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
125: Compounds 3721 to 3750 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-125 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 126: Compounds 3751 to 3780 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-126 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
127: Compounds 3781 to 3810 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-127 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 128: Compounds 3810 to 3840 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-128 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
129: Compounds 3841 to 3870 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-129 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 130: Compounds 3871 to 3900 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-130 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
131: Compounds 3901 to 3930 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-131 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 132: Compounds 3931 to 3960 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-132 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A.
Table 133: Compounds 3961 to 3990 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-133 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 134: Compounds 3991 to 4020 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-134 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 135: Compounds 4021 to 4050 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-135 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 136: Compounds 4051 to 4080 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-136 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 137: Compounds 4081 to 4110 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-137 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 138: Compounds 4111 to 4140 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-138 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 139: Compounds 4141 to 4170 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-139 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 140: Compounds 4171 to 4200 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-140 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 141: Compounds 4201 to 4230 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-141 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 142: Compounds 4231 to 4260 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-142 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 143: Compounds 4261 to 4290 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-143 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 144: Compounds 4291 to 4320 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-144 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 145: Compounds 4321 to 4350 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-145 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 146: Compounds 4351 to 4380 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-146 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 147: Compounds 4381 to 4410 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-147 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 148: Compounds 4411 to 4440 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-148 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 148a: Compounds 4441 to 4470 of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-149 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 148b:
Compounds 4471 to 4500 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-150 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148c: Compounds 4501 to 4530 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-151 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148d: Compounds 4531 to 4560 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-152 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148e: Compounds 4561 to 4590 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-153 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148f: Compounds 4591 to 4620 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-154 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148g: Compounds 4621 to 4650 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-155 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148h: Compounds 4651 to 4680 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-156 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148i: Compounds 4681 to 4710 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-157 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148j: Compounds 4711 to 4740 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-158 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148k: Compounds 4741 to 4770 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-159 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148l: Compounds 4771 to 4800 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-160 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148m: Compounds 4801 to 4830 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-161 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148n: Compounds 4831 to 4860 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-162 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148o: Compounds 4861 to 4890 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-163 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148p: Compounds 4891 to 4920 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-164 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148q: Compounds 4921 to 4950 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-165 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148r: Compounds 4951 to 4980 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-166 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148s: Compounds 4981 to 5010 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-167 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148t: Compounds 5011 to 5040 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-168 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148u: Compounds 5041 to 5070 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-169 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148v: Compounds 5071 to 5100 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-170 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148w: Compounds 5101 to 5130 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-171 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148x: Compounds 5131 to 5160 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-172 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148y: Compounds 5161 to 5190 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-173 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148z: Compounds 5191 to 5220 of formula I, wherein X.sup.1, X.sup.2
and R.sup.1 are defined as in line P-174 of table P and the meaning
of R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148aa: Compounds 5221 to 5250 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-175 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148bb: Compounds 5251 to 5280 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-176 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 148cc: Compounds 5281 to 5310 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-177 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 148dd: Compounds 5311 to 5340 of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-178 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 148ee:
Compounds 5441 to 5370 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-179 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 148ff: Compounds 5371 to 5400 of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line
P-180 of table P and the meaning of R.sup.2 for each individual
compound corresponds in each case to one line of table A. Table
148gg: Compounds 5401 to 5430 of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-181 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A. Table 148hh: Compounds 5431 to 5460 of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-182 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A. Table 148ii: Compounds 5461 to 5490 of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-183 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A. Table 148jj:
Compounds 5491 to 5520 of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-184 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A. Table 149: Compounds 1a to 30a of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-1 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 150:
Compounds 31a to 60a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-2 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 151: Compounds 61a to 90a of formula I,
wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-3 of
table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 152:
Compounds 91a to 120a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-4 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 153: Compounds 121a to 150a of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-5
of table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 154:
Compounds 151a to 180a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-6 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 155: Compounds 181a to 210a of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-7
of table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 156:
Compounds 211a to 240a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-8 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 157: Compounds 241a to 270a of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-9
of table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 158:
Compounds 271a to 300a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-10 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 159: Compounds 301a to 330a of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-11
of table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 160:
Compounds 331a to 360a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-12 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 161: Compounds 361a to 390a of formula
I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-13
of table P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 162:
Compounds 391a to 420a of formula I, wherein X
.sup.1, X.sup.2 and R.sup.1 are defined as in line P-14 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 163: Compounds 421a to
450a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-15 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 164: Compounds 451a to 480a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-16 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 165: Compounds 481a to
510a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-17 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 166: Compounds 511a to 540a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-18 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 167: Compounds 541a to
570a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-19 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 168: Compounds 571a to 600a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-20 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 169: Compounds 601a to
630a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-21 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 170: Compounds 631a to 660a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-22 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 171: Compounds 661a to
690a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-23 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 172: Compounds 691a to 720a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-24 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 173: Compounds 721a to
750a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-25 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 174: Compounds 751a to 780a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-26 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 175: Compounds 781a to
810a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-27 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 176: Compounds 811a to 840a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-28 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 177: Compounds 841a to
870a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-29 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 178: Compounds 871a to 900a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-30 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 179: Compounds 901a to
930a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-31 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 180: Compounds 931a to 960a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-32 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 181: Compounds 961a to
990a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined
as in line P-33 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 182: Compounds 991a to 1020a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-34 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 183: Compounds 1021a to
1050a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-35 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 184: Compounds 1051a to 1080a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-36 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 185: Compounds 1081a to
1110a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-37 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 186: Compounds 1111a to 1140a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-38 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 187: Compounds 1141a to
1170a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-39 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 188: Compounds 1171a to 1200a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-40 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 189: Compounds 1201a to
1230a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-41 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 190: Compounds 1231a to 1260a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-42 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 191: Compounds 1261a to
1290a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-43 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 192: Compounds 1291a to 1320a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-44 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 193: Compounds 1321a to
1350a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-45 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 194: Compounds 1351a to 1380a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-46 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 195: Compounds 1381a to
1410a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-47 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 196: Compounds 1411a to 1440a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-48 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 197: Compounds 1441a to
1470a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-49 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 198: Compounds 1471a to 1500a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-50 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 199: Compounds 1501a to
1530a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-51 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 200: Compounds 1531a to 1560a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-52 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 201: Compounds 1561a to
1590a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-53 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 202: Compounds 1591a to 1620a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-54 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 203: Compounds 1621a to
1650a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-55 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 204: Compounds 1651a to 1680a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-56 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 205: Compounds 1681a to
1710a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-57 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 206: Compounds 1711a to 1740a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-58 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 207: Compounds 1741a to
1770a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-59 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 208: Compounds 1771a to 1800a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-60 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 209: Compounds 1801a to
1830a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-61 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 210: Compounds 1831a to 1860a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-62 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 211: Compounds 1861a to
1890a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-63 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 212: Compounds 1891a to 1920a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-64 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 213: Compounds 1921a to
1950a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-65 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 214: Compounds 1951a to 1980a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-66 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 215: Compounds 1981a to
2010a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-67 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 216: Compounds 2011a to 2040a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-68 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 217: Compounds 2041a to
2070a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-69 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 218: Compounds 2071a to 2100a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-70 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 219: Compounds 2101a to
2130a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-71 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 220: Compounds 2131a to 2160a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-72 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 221: Compounds 2161a to
2190a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-73 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 222: Compounds 2191a to 2220a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-74 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 223: Compounds 2221a to
2250a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-75 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 224: Compounds 2251a to 2280a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-76 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 225: Compounds 2281a to
2310a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-77 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 226: Compounds 2311a to 2340a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-78 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 227: Compounds 2341a to
2370a of formula I, wherein X
.sup.1, X.sup.2 and R.sup.1 are defined as in line P-79 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 228: Compounds 2371a to
2400a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-80 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 229: Compounds 2401a to 2430a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-81 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 230: Compounds 2431a to
2460a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-82 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 231: Compounds 2461a to 2490a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-83 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 232: Compounds 2491a to
2520a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-84 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 233: Compounds 2521a to 2550a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-85 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 234: Compounds 2551a to
2580a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-86 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 235: Compounds 2581a to 2610a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-87 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 236: Compounds 2611a to
2640a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-88 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 237: Compounds 2641a to 2670a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-89 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 238: Compounds 2671a to
2700a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-90 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 239: Compounds 2701a to 2730a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-91 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 240: Compounds 2731a to
2760a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-92 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 241: Compounds 2761a to 2790a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-93 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 242: Compounds 2791a to
2820a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-94 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 243: Compounds 2821a to 2850a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-95 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 244: Compounds 2851a to
2880a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-96 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 245: Compounds 2881a to 2910a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-97 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 246: Compounds 2911a to
2940a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-98 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 247: Compounds 2941a to 2970a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-99 of table P
and the meaning of R.sup.2 for each individual compound corresponds
in each case to one line of table A1. Table 248: Compounds 2971a to
3000a of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are
defined as in line P-100 of table P and the meaning of R.sup.2 for
each individual compound corresponds in each case to one line of
table A1. Table 249: Compounds 3001a to 3030a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-101 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 250:
Compounds 3031a to 3060a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-102 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 251: Compounds 3061a to 3090a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-103 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 252: Compounds 3091a to 3120a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-104 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 253:
Compounds 3121a to 3150a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-105 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 254: Compounds 3151a to 3180a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-106 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 255: Compounds 3181a to 3210a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-107 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 256:
Compounds 3211a to 3240a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-108 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 257: Compounds 3241a to 3270a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-109 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 258: Compounds 3271a to 3300a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-110 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 259:
Compounds 3301a to 3330a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-111 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 260: Compounds 3331a to 3360a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-112 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 261: Compounds 3361a to 3390a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-113 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 262:
Compounds 3391a to 3420a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-114 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 263: Compounds 3421a to 3450a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-115 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 264: Compounds 3451a to 3480a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-116 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 265:
Compounds 3481a to 3510a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-117 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 266: Compounds 3510a to 3540a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-118 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 267: Compounds 3541a to 3570a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-119 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 268:
Compounds 3571a to 3600a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-120 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 269: Compounds 3601a to 3630a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-121 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 270: Compounds 3631a to 3660a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-122 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 271:
Compounds 3661a to 3690a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-123 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 272: Compounds 3691a to 3720a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-124 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 273: Compounds 3721a to 3750a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-125 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 274:
Compounds 3751a to 3780a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-126 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 275: Compounds 3781a to 3810a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-127 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 276: Compounds 3810a to 3840a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-128 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 277:
Compounds 3841a to 3870a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-129 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 278: Compounds 3871a to 3900a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-130 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 279: Compounds 3901a to 3930a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-131 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 280:
Compounds 3931a to 3960a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-132 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 281: Compounds 3961a to 3990a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-133 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 282: Compounds 3991a to 4020a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-134 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 283:
Compounds 4021a to 4050a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-135 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 284: Compounds 4051a to 4080a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-136 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 285: Compounds 4081a to 4110a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-137 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 286:
Compounds 4111a to 4140a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-138 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 287: Compounds 4141a to 4170a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-139 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 288: Compounds 4171a to 4200a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-140 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 289:
Compounds 4201a to 4230a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-141 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 290: Compounds 4231a to 4260a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-142 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 291: Compounds 4261a to 4290a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-143 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1.
Table 292: Compounds 4291a to 4320a of formula I, wherein X.sup.1,
X.sup.2 and R.sup.1 are defined as in line P-144 of table P and the
meaning of R.sup.2 for each individual compound corresponds in each
case to one line of table A1. Table 293: Compounds 4321a to 4350a
of formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as
in line P-145 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 294: Compounds 4351a to 4380a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-146 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 295:
Compounds 4381a to 4410a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-147 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296: Compounds 4411a to 4440a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-148 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296a: Compounds 4441a to 4470a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-149 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296b:
Compounds 4471a to 4500a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-150 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296c: Compounds 4501a to 4530a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-151 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296d: Compounds 4531a to 4560a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-152 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296e:
Compounds 4561a to 4590a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-153 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296f: Compounds 4591a to 4620a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-154 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296g: Compounds 4621a to 4650a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-155 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296h:
Compounds 4651a to 4680a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-156 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296i: Compounds 4681a to 4710a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-157 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296j: Compounds 4711a to 4740a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-158 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296k:
Compounds 4741a to 4770a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-159 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296l: Compounds 4771a to 4800a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-160 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296m: Compounds 4801a to 4830a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-161 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296n:
Compounds 4831a to 4860a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-162 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296o: Compounds 4861a to 4890a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-163 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296p: Compounds 4891a to 4920a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-164 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296q:
Compounds 4921a to 4950a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-165 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296r: Compounds 4951a to 4980a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-166 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296s: Compounds 4981a to 5010a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-167 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296t:
Compounds 5011a to 5040a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-168 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296u: Compounds 5041a to 5070a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-169 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296v: Compounds 5071a to 5100a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-170 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296w:
Compounds 5101a to 5130a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-171 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296x: Compounds 5131a to 5160a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-172 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296y: Compounds 5161a to 5190a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-173 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296z:
Compounds 5191a to 5220a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-174 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296aa: Compounds 5221a to 5250a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-175 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296bb: Compounds 5251a to 5280a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-176 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296cc:
Compounds 5281a to 5310a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-177 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296dd: Compounds 5311a to 5340a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-178 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296ee: Compounds 5441a to 5370a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-179 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296ff:
Compounds 5371a to 5400a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-180 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296gg: Compounds 5401a to 5430a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-181 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1. Table 296hh: Compounds 5431a to 5460a of formula I, wherein
X.sup.1, X.sup.2 and R.sup.1 are defined as in line P-182 of table
P and the meaning of R.sup.2 for each individual compound
corresponds in each case to one line of table A1. Table 296ii:
Compounds 5461a to 5490a of formula I, wherein X.sup.1, X.sup.2 and
R.sup.1 are defined as in line P-183 of table P and the meaning of
R.sup.2 for each individual compound corresponds in each case to
one line of table A1. Table 296jj: Compounds 5491a to 5520a of
formula I, wherein X.sup.1, X.sup.2 and R.sup.1 are defined as in
line P-184 of table P and the meaning of R.sup.2 for each
individual compound corresponds in each case to one line of table
A1.
TABLE-US-00004 TABLE A line R.sup.2 A-1 CH.sub.3 A-2
CH.sub.2CH.sub.3 A-3 CH.sub.2CH.sub.2CH.sub.3 A-4
CH(CH.sub.3).sub.2 A-5 C(CH.sub.3).sub.3 A-6
CH.sub.2CH.sub.2CH.sub.2CH.sub.3 A-7 C.sub.3H.sub.5 A-8
C.sub.5H.sub.9 A-9 C.sub.6H.sub.11 A-10 C.sub.6H.sub.5 A-11
CH.sub.2--C.sub.6H.sub.5 A-12 CH.sub.2--C.sub.3H.sub.5 A-13
CF.sub.3 A-14 CHF.sub.2 A-15 CH.sub.2--CN A-16 CH.sub.2CH.sub.2--CN
A-17 C.ident.CH A-18 C.ident.CCH.sub.3 A-19 CH.sub.2C.ident.CH A-20
4-F--C.sub.6H.sub.4 A-21 4-Cl--C.sub.6H.sub.4 A-22
2,4-Cl.sub.2--C.sub.6H.sub.3 A-23 2,4,6-Cl.sub.3--C.sub.6H.sub.2
A-24 2,4,6-F.sub.3--C.sub.6H.sub.2 A-25 CH.sub.2--C.sub.6H.sub.5
A-26 CH.sub.2-(4-F--C.sub.6H.sub.4) A-27
CH.sub.2-(4-Cl--C.sub.6H.sub.4) A-28 CH.dbd.CH--C.sub.6H.sub.5 A-29
CH.dbd.CH-(4-F--C.sub.6H.sub.4) A-30
CH.dbd.CH-(4-Cl--C.sub.6H.sub.4)
TABLE-US-00005 TABLE A1 line R.sup.2 A1-1 CH.sub.2CH.dbd.CH.sub.2
A1-2 CH.sub.2C.ident.CCH.sub.3 A1-3 CH.sub.2OCH.sub.3 A1-4
CH.sub.2OC.sub.2H.sub.5 A1-5 CH.sub.2CH.sub.2OCH.sub.3 A1-6
CH.sub.2C(CH.sub.3).dbd.CH.sub.2 A1-7
CH.sub.2-(4-OCH.sub.3--C.sub.6H.sub.4) A1-8
CH.sub.2-(4-CH.sub.3--C.sub.6H.sub.4) A1-9 CH.sub.2Cl A1-10
CH.sub.2CH.sub.2Cl A1-11 CH.sub.2C.ident.CCH.sub.2CH.sub.3 A1-12
CH.sub.2C.ident.CCH(CH.sub.3).sub.2 A1-13
CH.sub.2C.ident.CC(CH.sub.3).sub.3 A1-14 CH.sub.2CH.sub.2CH.sub.2Cl
A1-15 CH.sub.2C.ident.CCl A1-16 CH.sub.2CH.dbd.CHCH.sub.3 A1-17
CH.sub.2CH.dbd.CHCH.sub.2CH.sub.3 A1-18
CH.sub.2C.ident.CC(CH.sub.3).sub.3 A1-19 C(CH.sub.3).dbd.CH.sub.2
A1-20 CH.sub.2CH.sub.2CF.sub.3 A1-21 CH(CH.sub.3)CH.sub.2CH.sub.3
A1-22 CH.sub.2CH(CH.sub.3).sub.2 A1-23
CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.3 A1-24
CH.sub.2CH.sub.2CH(CH.sub.3).sub.2 A1-25
CH.sub.2CH(OCH.sub.3)CH.sub.3 A1-26
CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.3 A1-27
CH.sub.2(2,4-Cl.sub.2--C.sub.6H.sub.3) A1-28
CH.sub.2C(Cl).dbd.CH.sub.2 A1-29 CH.sub.2CH.dbd.CHCl A1-30
CH.sub.2C.ident.C--CH.sub.2OCH.sub.3
[0115] The compounds I and VIII, respectively, and the compositions
according to the invention, respectively, are suitable as
fungicides. They are distinguished by an outstanding effectiveness
against a broad spectrum of phytopathogenic fungi, including
soil-borne fungi, which derive especially from the classes of the
Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes),
Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and
Deuteromycetes (syn. Fungi imperfecti). Some are systemically
effective and they can be used in crop protection as foliar
fungicides, fungicides for seed dressing and soil fungicides.
Moreover, they are suitable for controlling harmful fungi, which
inter alia occur in wood or roots of plants.
[0116] The compounds I and VIII, respectively, and the compositions
according to the invention are particularly important in the
control of a multitude of phytopathogenic fungi on various
cultivated plants, such as cereals, e.g. wheat, rye, barley,
triticale, oats or rice; beet, e.g. sugar beet or fodder beet;
fruits, such as pomes, stone fruits or soft fruits, e.g. apples,
pears, plums, peaches, almonds, cherries, strawberries,
raspberries, blackberries or gooseberries; leguminous plants, such
as lentils, peas, alfalfa or soybeans; oil plants, such as rape,
mustard, olives, sunflowers, coconut, cocoa beans, castor oil
plants, oil palms, ground nuts or soybeans; cucurbits, such as
squashes, cucumber or melons; fiber plants, such as cotton, flax,
hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or
mandarins; vegetables, such as spinach, lettuce, asparagus,
cabbages, carrots, onions, tomatoes, potatoes, cucurbits or
paprika; lauraceous plants, such as avocados, cinnamon or camphor;
energy and raw material plants, such as corn, soybean, rape, sugar
cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines
(table grapes and grape juice grape vines); hop; turf; sweet leaf
(also called Stevia); natural rubber plants or ornamental and
forestry plants, such as flowers, shrubs, broad-leaved trees or
evergreens, e.g. conifers; and on the plant propagation material,
such as seeds, and the crop material of these plants.
[0117] Preferably, compounds I and VIII, respectively, and
compositions thereof, respectively are used for controlling a
multitude of fungi on field crops, such as potatoes sugar beets,
tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans,
rape, legumes, sunflowers, coffee or sugar cane; fruits; vines;
ornamentals; or vegetables, such as cucumbers, tomatoes, beans or
squashes.
[0118] The term "plant propagation material" is to be understood to
denote all the generative parts of the plant such as seeds and
vegetative plant material such as cuttings and tubers (e.g.
potatoes), which can be used for the multiplication of the plant.
This includes seeds, roots, fruits, tubers, bulbs, rhizomes,
shoots, sprouts and other parts of plants, including seedlings and
young plants, which are to be transplanted after germination or
after emergence from soil. These young plants may also be protected
before transplantation by a total or partial treatment by immersion
or pouring.
[0119] Preferably, treatment of plant propagation materials with
compounds I and VIII, respectively, and compositions thereof,
respectively, is used for controlling a multitude of fungi on
cereals, such as wheat, rye, barley and oats; rice, corn, cotton
and soybeans.
[0120] The term "cultivated plants" is to be understood as
including plants which have been modified by breeding, mutagenesis
or genetic engineering including but not limiting to agricultural
biotech products on the market or in development (cf.
http://www.bio.org/speeches/pubs/er/agri_products.asp). Genetically
modified plants are plants, which genetic material has been so
modified by the use of recombinant DNA techniques that under
natural circumstances cannot readily be obtained by cross breeding,
mutations or natural recombination. Typically, one or more genes
have been integrated into the genetic material of a genetically
modified plant in order to improve certain properties of the plant.
Such genetic modifications also include but are not limited to
targeted post-translational modification of protein(s), oligo- or
polypeptides e.g. by glycosylation or polymer additions such as
prenylated, acetylated or farnesylated moieties or PEG
moieties.
[0121] Plants that have been modified by breeding, mutagenesis or
genetic engineering, e.g. have been rendered tolerant to
applications of specific classes of herbicides, such as auxin
herbicides such as dicamba or 2,4-D; bleacher herbicides such as
hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene
desaturase (PDS) inhibittors; acetolactate synthase (ALS)
inhibitors such as sulfonyl ureas or imidazolinones;
enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such
as glyphosate; glutamine synthetase (GS) inhibitors such as
glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid
biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase)
inhibitors; or oxynil (i.e. bromoxynil or ioxynil) herbicides as a
result of conventional methods of breeding or genetic engineering.
Furthermore, plants have been made resistant to multiple classes of
herbicides through multiple genetic modifications, such as
resistance to both glyphosate and glufosinate or to both glyphosate
and a herbicide from another class such as ALS inhibitors, HPPD
inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide
resistance technologies are e.g. described in Pest Managem. Sci.
61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61,
2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108;
Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185;
and references quoted therein. Several cultivated plants have been
rendered tolerant to herbicides by conventional methods of breeding
(mutagenesis), e.g. Clearfield.RTM. summer rape (Canola, BASF SE,
Germany) being tolerant to imidazolinones, e.g. imazamox, or
ExpressSun.RTM. sunflowers (DuPont, USA) being tolerant to sulfonyl
ureas, e.g. tribenuron. Genetic engineering methods have been used
to render cultivated plants such as soybean, cotton, corn, beets
and rape, tolerant to herbicides such as glyphosate and
glufosinate, some of which are commercially available under the
trade names RoundupReady.RTM. (glyphosate-tolerant, Monsanto,
U.S.A.), Cultivance.RTM. (imidazolinone tolerant, BASF SE, Germany)
and LibertyLink.RTM. (glufosinate-tolerant, Bayer CropScience,
Germany).
[0122] Furthermore, plants are also covered that are by the use of
recombinant DNA techniques capable to synthesize one or more
insecticidal proteins, especially those known from the bacterial
genus Bacillus, particularly from Bacillus thuringiensis, such as
5-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b),
CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins
(VIP), e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of
bacteria colonizing nematodes, e.g. Photorhabdus spp. or
Xenorhabdus spp.; toxins produced by animals, such as scorpion
toxins, arachnid toxins, wasp toxins, or other insect-specific
neurotoxins; toxins produced by fungi, such Streptomycetes toxins,
plant lectins, such as pea or barley lectins; agglutinins;
proteinase inhibitors, such as trypsin inhibitors, serine protease
inhibitors, patatin, cystatin or papain inhibitors;
ribosome-inactivating proteins (RIP), such as ricin, maize-RIP,
abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such
as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase,
cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion
channel blockers, such as blockers of sodium or calcium channels;
juvenile hormone esterase; diuretic hormone receptors (helicokinin
receptors); stilben synthase, bibenzyl synthase, chitinases or
glucanases. In the context of the present invention these
insecticidal proteins or toxins are to be understood expressly also
as pre-toxins, hybrid proteins, truncated or otherwise modified
proteins. Hybrid proteins are characterized by a new combination of
protein domains, (see, e.g. WO 02/015701). Further examples of such
toxins or genetically modified plants capable of synthesizing such
toxins are disclosed, e.g., in EP-A 374 753, WO 93/007278, WO
95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073.
The methods for producing such genetically modified plants are
generally known to the person skilled in the art and are described,
e.g. in the publications mentioned above. These insecticidal
proteins contained in the genetically modified plants impart to the
plants producing these proteins tolerance to harmful pests from all
taxonomic groups of athropods, especially to beetles (Coeloptera),
two-winged insects (Diptera), and moths (Lepidoptera) and to
nematodes (Nematoda). Genetically modified plants capable to
synthesize one or more insecticidal proteins are, e.g., described
in the publications mentioned above, and some of which are
commercially available such as YieldGard.RTM. (corn cultivars
producing the Cry1Ab toxin), YieldGard.RTM. Plus (corn cultivars
producing Cry1Ab and Cry3Bb1 toxins), Starlink.RTM. (corn cultivars
producing the Cry9c toxin), Herculex.RTM. RW (corn cultivars
producing Cry34Ab1, Cry35Ab1 and the enzyme
Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN.RTM. 33B
(cotton cultivars producing the Cry1Ac toxin), Bollgard.RTM. I
(cotton cultivars producing the Cry1Ac toxin), Bollgard.RTM. II
(cotton cultivars producing Cry1Ac and Cry2Ab2 toxins); VIPCOT.RTM.
(cotton cultivars producing a VIP-toxin); NewLeaf.RTM. (potato
cultivars producing the Cry3A toxin); BtXtra.RTM., NatureGard.RTM.,
KnockOut.RTM., BiteGard.RTM., Protecta.RTM., Bt11 (e.g.
Agrisure.RTM. CB) and Bt176 from Syngenta Seeds SAS, France, (corn
cultivars producing the Cry1Ab toxin and PAT enyzme), MIR604 from
Syngenta Seeds SAS, France (corn cultivars producing a modified
version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from
Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1
toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton
cultivars producing a modified version of the Cry1Ac toxin) and
1507 from Pioneer Overseas Corporation, Belgium (corn cultivars
producing the Cry1F toxin and PAT enzyme).
[0123] Furthermore, plants are also covered that are by the use of
recombinant DNA techniques capable to synthesize one or more
proteins to increase the resistance or tolerance of those plants to
bacterial, viral or fungal pathogens. Examples of such proteins are
the so-called "pathogenesis-related proteins" (PR proteins, see,
e.g. EP-A 392 225), plant disease resistance genes (e.g. potato
cultivars, which express resistance genes acting against
Phytophthora infestans derived from the mexican wild potato Solanum
bulbocastanum) or T4-lysozym (e.g. potato cultivars capable of
synthesizing these proteins with increased resistance against
bacteria such as Erwinia amylvora). The methods for producing such
genetically modified plants are generally known to the person
skilled in the art and are described, e.g. in the publications
mentioned above.
[0124] Furthermore, plants are also covered that are by the use of
recombinant DNA techniques capable to synthesize one or more
proteins to increase the productivity (e.g. bio mass production,
grain yield, starch content, oil content or protein content),
tolerance to drought, salinity or other growth-limiting
environmental factors or tolerance to pests and fungal, bacterial
or viral pathogens of those plants.
[0125] Furthermore, plants are also covered that contain by the use
of recombinant DNA techniques a modified amount of substances of
content or new substances of content, specifically to improve human
or animal nutrition, e.g. oil crops that produce health-promoting
long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids
(e.g. Nexera.RTM. rape, DOW Agro Sciences, Canada).
[0126] Furthermore, plants are also covered that contain by the use
of recombinant DNA techniques a modified amount of substances of
content or new substances of content, specifically to improve raw
material production, e.g. potatoes that produce increased amounts
of amylopectin (e.g. Amflora.RTM. potato, BASF SE, Germany). The
compounds I and VIII, respectively, and compositions thereof,
respectively, are particularly suitable for controlling the
following plant diseases: Albugo spp. (white rust) on ornamentals,
vegetables (e.g. A. candida) and sunflowers (e.g. A. tragopogonis);
Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A.
brassicola or brassicae), sugar beets (A. tenuis), fruits, rice,
soybeans, potatoes (e.g. A. solani or A. alternata), tomatoes (e.g.
A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar
beets and vegetables; Ascochyta spp. on cereals and vegetables,
e.g. A. tritici (anthracnose) on wheat and A. hordei on barley;
Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g.
Southern leaf blight (D. maydis) or Northern leaf blight (B.
zeicola) on corn, e.g. spot blotch (B. sorokiniana) on cereals and
e.g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe)
graminis (powdery mildew) on cereals (e.g. on wheat or barley);
Botrytis cinerea (teleomorph: Botryotinia fuckliana: grey mold) on
fruits and berries (e.g. strawberries), vegetables (e.g. lettuce,
carrots, celery and cabbages), rape, flowers, vines, forestry
plants and wheat; Bremia lactucae (downy mildew) on lettuce;
Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved
trees and evergreens, e.g. C. ulmi (Dutch elm disease) on elms;
Cercospora spp. (Cercospora leaf spots) on corn (e.g. Gray leaf
spot: C. zeae-maydis), rice, sugar beets (e.g. C. beticola), sugar
cane, vegetables, coffee, soybeans (e.g. C. solina or C. kikuchli)
and rice; Cladosporium spp. on tomatoes (e.g. C. fulvum: leaf mold)
and cereals, e.g. C. herbarum (black ear) on wheat; Claviceps
purpurea (ergot) on cereals; Cochliobolus (anamorph:
Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C.
carbonum), cereals (e.g. C. sativus, anamorph: B. sorokiniana) and
rice (e.g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum
(teleomorph: Glomerella) spp. (anthracnose) on cotton (e.g. C.
gossypii), corn (e.g. C. graminicola: Anthracnose stalk rot), soft
fruits, potatoes (e.g. C. coccodes: black dot), beans (e.g. C.
lindemuthianum) and soybeans (e.g. C. truncatum or C.
gloeosporiodes); Corticium spp., e.g. C. sasakii blight) on rice;
Corynespora cassiicoia (leaf spots) on soybeans and ornamentals;
Cycloconium spp., e.g. C. oleaginum on olive trees; Cylindrocarpon
spp. (e.g. fruit tree canker or young vine decline, teleomorph:
Nectria or Neonectna spp.) on fruit trees, vines (e.g. C.
liriodendri, teleomorph: Neonectria liriodendri: Black Foot
Disease) and ornamentals; Dematophora (teleomorph: Rosellinia)
necatrix (root and stem rot) on soybeans; Diaporthe spp., e.g. D.
phaseolorum (damping off) on soybeans; Drechslera (syn.
Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals,
such as barley (e.g. D. teres, net blotch) and wheat (e.g. D.
tritici-repentis: tan spot), rice and turf; Esca (dieback,
apoplexy) on vines, caused by Formitiporia (syn. Phellinus)
punctata, F mediterranea, Phaeomonielia chlamydospora (earlier
Phaeoacremonlum chlamydosporum), Phaeoacremonlum aleophilum and/or
Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyri), soft
fruits (E. veneta: anthracnose) and vines (E. ampelina:
anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp.
(black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar
beets (E. betae), vegetables (e.g. E. pisi), such as cucurbits
(e.g. E. cichoracearum), cabbages, rape (e.g. E. cruciferarum);
Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata,
syn. Libertelia blepharis) on fruit trees, vines and ornamental
woods; Exserohilum (syn. Helminthosporium) spp. on corn (e.g. E.
turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or
stem rot) on various plants, such as F. graminearum or F. culmorum
(root rot, scab or head blight) on cereals (e.g. wheat or barley),
F. oxysporum on tomatoes, F. solani on soybeans and F.
verticilliodes on corn; Gaeumannomyces graminis (take-all) on
cereals (e.g. wheat or barley) and corn; Gibberella spp. on cereals
(e.g. G. zeae) and rice (e.g. G. fujikuroi: Bakanae disease);
Glomerella angulata on vines, pome fruits and other plants and G.
gossypii on cotton; Grain-staining complex on rice; Guignardia
bewellii (black rot) on vines; Gymnosporangium spp. on rosaceous
plants and junipers, e.g. G. sabinae (rust) on pears;
Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus)
on corn, cereals and rice; Hemileia spp., e.g. H. vastatrix(coffee
leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium
vitis) on vines; Macrophomina phaseolina (syn. phaseoli) (root and
stem rot) on soybeans and cotton; Microdochium (syn. Fusarium)
nivale (pink snow mold) on cereals (e.g. wheat or barley);
Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp.,
e.g. M. laxa, M. fructicoia and M. fructigena (bloom and twig
blight, brown rot) on stone fruits and other rosaceous plants;
Mycosphaerella spp. on cereals, bananas, soft fruits and ground
nuts, such as e.g. M. graminicola (anamorph: Septoria tritici,
Septoria blotch) on wheat or M. fiiiensis (black Sigatoka disease)
on bananas; Peronospora spp. (downy mildew) on cabbage (e.g. P.
brassicae), rape (e.g. P. parasitica), onions (e.g. P. destructor),
tobacco (P. tabacina) and soybeans (e.g. P. manshurica); Phakopsora
pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora
spp. e.g. on vines (e.g. P. tracheiphda and P. tetraspora) and
soybeans (e.g. P. gregata: stem rot); Phoma lingam (root and stem
rot) on rape and cabbage and P. betae (root rot, leaf spot and
damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines
(e.g. P. viticola: can and leaf spot) and soybeans (e.g. stem rot:
P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis
(brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit
and stem root) on various plants, such as paprika and cucurbits
(e.g. P. capsici), soybeans (e.g. P. megasperma, syn. P. sojae),
potatoes and tomatoes (e.g. P. infestans: late blight) and
broad-leaved trees (e.g. P. ramorum: sudden oak death);
Plasmodiophora brassicae (club root) on cabbage, rape, radish and
other plants; Plasmopara spp., e.g. P. viticola (grapevine downy
mildew) on vines and P. halstedii on sunflowers; Podosphaera spp.
(powdery mildew) on rosaceous plants, hop, pome and soft fruits,
e.g. P. leucotricha on apples; Polymyxa spp., e.g. on cereals, such
as barley and wheat (P. graminis) and sugar beets (P. betae) and
thereby transmitted viral diseases; Pseudocercosporella
herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on
cereals, e.g. wheat or barley; Pseudoperonospora (downy mildew) on
various plants, e.g. P. cubensis on cucurbits or P. humili on hop;
Pseudopezicula tracheiphda (red fire disease or `rotbrenner`,
anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various
plants, e.g. P. triticina (brown or leaf rust), P. striiformis
(stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem
or black rust) or P. recondita (brown or leaf rust) on cereals,
such as e.g. wheat, barley or rye, P. kuehnli (orange rust) on
sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph:
Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net
blotch) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph:
Magnaporthe grisea, rice blast) on rice and P. gnisea on turf and
cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat,
cotton, rape, sunflowers, soybeans, sugar beets, vegetables and
various other plants (e.g. P. ultirnum or P. aphanidermatum);
Ramulana spp., e.g. R. collocygni (Ramularia leaf spots,
Physiological leaf spots) on barley and R. beticola on sugar beets;
Rhizoctoma spp. on cotton, rice, potatoes, turf, corn, rape,
potatoes, sugar beets, vegetables and various other plants, e.g. R.
solani (root and stem rot) on soybeans, R. solani (sheath blight)
on rice or R. cerealis (Rhizoctonia spring blight) on wheat or
barley; Rhizopus stolonifer (black mold, soft rot) on strawberries,
carrots, cabbage, vines and tomatoes; Rhynchosporium secalis
(scald) on barley, rye and triticafe; Sarocladium oryzae and S.
attenuatum (sheath rot) on rice; Sclerotima spp. (stem rot or white
mold) on vegetables and field crops, such as rape, sunflowers (e.g.
S. sclerotiorum) and soybeans (e.g. S. rolfsll or S. sclerotiorum);
Septona spp. on various plants, e.g. S. glycines (brown spot) on
soybeans, S. tritici (Septoria blotch) on wheat and S. (syn.
Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula
(syn. Erysiphe) necator (powdery mildew, anamorph: Oldium tuckeri)
on vines; Setospaena spp. (leaf blight) on corn (e.g. S. turcicum,
syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut)
on corn, (e.g. S. reiliana: head smut), sorghum and sugar cane;
Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora
subterranea (powdery scab) on potatoes and thereby transmitted
viral diseases; Stagonospora spp. on cereals, e.g. S. nodorum
(Stagonospora blotch, teleomorph: Leptosphaena [syn. Phaeosphaena]
nodorum) on wheat; Synchytrium endobioticum on potatoes (potato
wart disease); Taphnna spp., e.g. T deformans (leaf curl disease)
on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp.
(black root rot) on tobacco, pome fruits, vegetables, soybeans and
cotton, e.g. T. basicola (syn. Chalara elegans); Tilletia spp.
(common bunt or stinking smut) on cereals, such as e.g. T. tritici
(syn. T caries, wheat bunt) and T. controversa (dwarf bunt) on
wheat; Typhula incarnata (grey snow mold) on barley or wheat;
Urocystis spp., e.g. U. occulta (stem smut) on rye; Uromyces spp.
(rust) on vegetables, such as beans (e.g. U. appendiculatus, syn.
U. phaseoli) and sugar beets (e.g. U. betae); Ustilago spp. (loose
smut) on cereals (e.g. U. nuda and U. avaenae), corn (e.g. U.
maydis: corn smut) and sugar cane; Ventuna spp. (scab) on apples
(e.g. V. inaequalis) and pears; and Verticillium spp. (wilt) on
various plants, such as fruits and ornamentals, vines, soft fruits,
vegetables and field crops, e.g. V. dahliae on strawberries, rape,
potatoes and tomatoes.
[0127] The compounds I and VIII, respectively, and compositions
thereof, respectively, are also suitable for controlling harmful
fungi in the protection of stored products or harvest and in the
protection of materials. The term "protection of materials" is to
be understood to denote the protection of technical and non-living
materials, such as adhesives, glues, wood, paper and paperboard,
textiles, leather, paint dispersions, plastics, coiling lubricants,
fiber or fabrics, against the infestation and destruction by
harmful microorganisms, such as fungi and bacteria. As to the
protection of wood and other materials, the particular attention is
paid to the following harmful fungi: Ascomycetes such as Ophiostoma
spp., Ceratocystis spp., Aureobasldlum pullulans, Sclerophoma spp.,
Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.;
Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum
spp., Lentinus spp., Pleurotus spp., Pona spp., Serpula spp. and
Tyromyces spp., Deuteromycetes such as Aspergillus spp.,
Cladosporium spp., Penicillium spp., Trichorma spp., Alternana
spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., and in
addition in the protection of stored products and harvest the
following yeast fungi are worthy of note: Candida spp. and
Saccharomyces cerevisae.
[0128] The compounds I and VIII, respectively, and compositions
thereof, resepectively, may be used for improving the health of a
plant. The invention also relates to a method for improving plant
health by treating a plant, its propagation material and/or the
locus where the plant is growing or is to grow with an effective
amount of compounds I and VIII, respectively, and compositions
thereof, respectively.
[0129] The term "plant health" is to be understood to denote a
condition of the plant and/or its products which is determined by
several indicators alone or in combination with each other such as
yield (e.g. increased biomass and/or increased content of valuable
ingredients), plant vigor (e.g. improved plant growth and/or
greener leaves ("greening effect")), quality (e.g. improved content
or composition of certain ingredients) and tolerance to abiotic
and/or biotic stress. The above identified indicators for the
health condition of a plant may be interdependent or may result
from each other.
[0130] The compounds of formula I and VIII, respectively, can be
present in different crystal modifications whose biological
activity may differ. They are likewise subject matter of the
present invention.
[0131] The compounds I and VIII, respectively, are employed as such
or in form of compositions by treating the fungi or the plants,
plant propagation materials, such as seeds, soil, surfaces,
materials or rooms to be protected from fungal attack with a
fungicidally effective amount of the active substances. The
application can be carried out both before and after the infection
of the plants, plant propagation materials, such as seeds, soil,
surfaces, materials or rooms by the fungi.
[0132] Plant propagation materials may be treated with compounds I
and VIII, respectively, as such or a composition comprising at
least one compound I and VIII, respectively, prophylactically
either at or before planting or transplanting.
[0133] The invention also relates to agrochemical compositions
comprising an auxiliary and at least one compound I or VIII,
respectively, according to the invention.
[0134] An agrochemical composition comprises a fungicidally
effective amount of a compound I or VIII, respectively. The term
"effective amount" denotes an amount of the composition or of the
compounds I or VIII, respectively, which is sufficient for
controlling harmful fungi on cultivated plants or in the protection
of materials and which does not result in a substantial damage to
the treated plants. Such an amount can vary in a broad range and is
dependent on various factors, such as the fungal species to be
controlled, the treated cultivated plant or material, the climatic
conditions and the specific compound I or VIII, respectively,
used.
[0135] The compounds I and VIII, respectively, their N-oxides and
salts can be converted into customary types of agrochemical
compositions, e.g. solutions, emulsions, suspensions, dusts,
powders, pastes, granules, pressings, capsules, and mixtures
thereof. Examples for composition types are suspensions (e.g. SC,
OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW,
EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable
powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB,
DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles
(e.g. LN), as well as gel formulations for the treatment of plant
propagation materials such as seeds (e.g. GF). These and further
compositions types are defined in the "Catalogue of pesticide
formulation types and international coding system", Technical
Monograph No. 2, 6th Ed. May 2008, CropLife International.
[0136] The compositions are prepared in a known manner, such as
described by Mollet and Grubemann, Formulation technology, Wiley
VCH, Weinheim, 2001; or Knowles, New developments in crop
protection product formulation, Agrow Reports DS243, T&F
Informa, London, 2005.
[0137] Suitable auxiliaries are solvents, liquid carriers, solid
carriers or fillers, surfactants, dispersants, emulsifiers,
wetters, adjuvants, solubilizers, penetration enhancers, protective
colloids, adhesion agents, thickeners, humectants, repellents,
attractants, feeding stimulants, compatibilizers, bactericides,
anti-freezing agents, anti-foaming agents, colorants, tackifiers
and binders.
[0138] Suitable solvents and liquid carriers are water and organic
solvents, such as mineral oil fractions of medium to high boiling
point, e.g. kerosene, diesel oil; oils of vegetable or animal
origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene,
paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols,
e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol;
glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates,
carbonates, fatty acid esters, gamma-butyrolactone; fatty acids;
phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid
dimethylamides; and mixtures thereof.
[0139] Suitable solid carriers or fillers are mineral earths, e.g.
silicates, silica gels, talc, kaolins, limestone, lime, chalk,
clays, dolomite, diatomaceous earth, bentonite, calcium sulfate,
magnesium sulfate, magnesium oxide; polysaccharides, e.g.
cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium
phosphate, ammonium nitrate, ureas; products of vegetable origin,
e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and
mixtures thereof.
[0140] Suitable surfactants are surface-active compounds, such as
anionic, cationic, nonionic and amphoteric surfactants, block
polymers, polyelectrolytes, and mixtures thereof. Such surfactants
can be used as emusifier, dispersant, solubilizer, wetter,
penetration enhancer, protective colloid, or adjuvant. Examples of
surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers &
Detergents, McCutcheon's Directories, Glen Rock, USA, 2008
(International Ed. or North American Ed.).
[0141] Suitable anionic surfactants are alkali, alkaline earth or
ammonium salts of sulfonates, sulfates, phosphates, carboxylates,
and mixtures thereof. Examples of sulfonates are
alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates,
lignine sulfonates, sulfonates of fatty acids and oils, sulfonates
of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols,
sulfonates of condensed naphthalenes, sulfonates of dodecyl- and
tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes,
sulfosuccinates or sulfosuccinamates. Examples of sulfates are
sulfates of fatty acids and oils, of ethoxylated alkylphenols, of
alcohols, of ethoxylated alcohols, or of fatty acid esters.
Examples of phosphates are phosphate esters. Examples of
carboxylates are alkyl carboxylates, and carboxylated alcohol or
alkylphenol ethoxylates.
[0142] Suitable nonionic surfactants are alkoxylates, N-subsituted
fatty acid amides, amine oxides, esters, sugar-based surfactants,
polymeric surfactants, and mixtures thereof. Examples of
alkoxylates are compounds such as alcohols, alkylphenols, amines,
amides, arylphenols, fatty acids or fatty acid esters which have
been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or
propylene oxide may be employed for the alkoxylation, preferably
ethylene oxide. Examples of N-subsititued fatty acid amides are
fatty acid glucamides or fatty acid alkanolamides. Examples of
esters are fatty acid esters, glycerol esters or monoglycerides.
Examples of sugar-based surfactants are sorbitans, ethoxylated
sorbitans, sucrose and glucose esters or alkylpolyglucosides.
Examples of polymeric surfactants are home- or copolymers of
vinylpyrrolidone, vinylalcohols, or vinylacetate.
[0143] Suitable cationic surfactants are quaternary surfactants,
for example quaternary ammonium compounds with one or two
hydrophobic groups, or salts of long-chain primary amines. Suitable
amphoteric surfactants are alkylbetains and imidazolines. Suitable
block polymers are block polymers of the A-B or A-B-A type
comprising blocks of polyethylene oxide and polypropylene oxide, or
of the A-B-C type comprising alkanol, polyethylene oxide and
polypropylene oxide. Suitable polyelectrolytes are polyacids or
polybases. Examples of polyacids are alkali salts of polyacrylic
acid or polyacid comb polymers. Examples of polybases are
polyvinylamines or polyethyleneamines.
[0144] Suitable adjuvants are compounds, which have a neglectable
or even no pesticidal activity themselves, and which improve the
biological performance of the compound I on the target. Examples
are surfactants, mineral or vegetable oils, and other auxilaries.
Further examples are listed by Knowles, Adjuvants and additives,
Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
[0145] Suitable thickeners are polysaccharides (e.g. xanthan gum,
carboxymethylcellulose), anorganic clays (organically modified or
unmodified), polycarboxylates, and silicates.
[0146] Suitable bactericides are bronopol and isothiazolinone
derivatives such as alkylisothiazolinones and
benzisothiazolinones.
[0147] Suitable anti-freezing agents are ethylene glycol, propylene
glycol, urea and glycerin.
[0148] Suitable anti-foaming agents are silicones, long chain
alcohols, and salts of fatty acids.
[0149] Suitable colorants (e.g. in red, blue, or green) are
pigments of low water solubility and water-soluble dyes. Examples
are inorganic colorants (e.g. iron oxide, titan oxide, iron
hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and
phthalocyanine colorants).
[0150] Suitable tackifiers or binders are polyvinylpyrrolidons,
polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or
synthetic waxes, and cellulose ethers.
[0151] Examples for composition types and their preparation
are:
i) Water-Soluble Concentrates (SL, LS)
[0152] 10-60 wt % of a compound I or VIII, respectively, and 5-15
wt % wetting agent (e.g. alcohol alkoxylates) are dissolved in
water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt
%. The active substance dissolves upon dilution with water.
ii) Dispersible Concentrates (DC)
[0153] 5-25 wt % of a compound I or VIII, respectively, and 1-10 wt
% dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic
solvent (e.g. cyclohexanone) ad 100 wt %. Dilution with water gives
a dispersion.
iii) Emulsifiable Concentrates (EC)
[0154] 15-70 wt % of a compound I or VIII, respectively, and 5-10
wt % emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor
oil ethoxylate) are dissolved in water-insoluble organic solvent
(e.g. aromatic hydrocarbon) ad 100 wt %. Dilution with water gives
an emulsion.
iv) Emulsions (EW, EO, ES)
[0155] 5-40 wt % of a compound I or VIII, respectively, and 1-10 wt
% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil
ethoxylate) are dissolved in 20-40 wt % water-insoluble organic
solvent (e.g. aromatic hydrocarbon). This mixture is introduced
into water ad 100 wt % by means of an emulsifying machine and made
into a homogeneous emulsion. Dilution with water gives an
emulsion.
v) Suspensions (SC, OD, FS)
[0156] In an agitated ball mill, 20-60 wt % of a compound I or
VIII, respectively, are comminuted with addition of 2-10 wt %
dispersants and wetting agents (e.g. sodium lignosulfonate and
alcohol ethoxylate), 0.1-2 wt % thickener (e.g. xanthan gum) and
water ad 100 wt % to give a fine active substance suspension.
Dilution with water gives a stable suspension of the active
substance. For FS type composition up to 40 wt % binder (e.g.
polyvinylalcohol) is added.
vi) Water-Dispersible Granules and Water-Soluble Granules (WG,
SG)
[0157] 50-80 wt % of a compound I or VIII, respectively, are ground
finely with addition of dispersants and wetting agents (e.g. sodium
lignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared as
water-dispersible or water-soluble granules by means of technical
appliances (e.g. extrusion, spray tower, fluidized bed). Dilution
with water gives a stable dispersion or solution of the active
substance.
vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP,
WS)
[0158] 50-80 wt % of a compound I or VIII, respectively, are ground
in a rotor-stator mill with addition of 1-5 wt % dispersants (e.g.
sodium lignosulfonate), 1-3 wt % wetting agents (e.g. alcohol
ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt %.
Dilution with water gives a stable dispersion or solution of the
active substance.
viii) Gel (GW, GF)
[0159] In an agitated ball mill, 5-25 wt % of a compound I or VIII,
respectively, are comminuted with addition of 3-10 wt % dispersants
(e.g. sodium lignosulfonate), 1-5 wt % thickener (e.g.
carboxymethylcellulose) and water ad 100 wt % to give a fine
suspension of the active substance. Dilution with water gives a
stable suspension of the active substance.
iv) Microemulsion (ME)
[0160] 5-20 wt % of a compound I or VIII, respectively, are added
to 5-30 wt % organic solvent blend (e.g. fatty acid dimethylamide
and cyclohexanone), 10-25 wt % surfactant blend (e.g. alcohol
ethoxylate and arylphenol ethoxylate), and water ad 100%. This
mixture is stirred for 1 h to produce spontaneously a
thermodynamically stable microemulsion.
iv) Microcapsules (CS)
[0161] An oil phase comprising 5-50 wt % of a compound I or VIII,
respectively, 0-40 wt % water insoluble organic solvent (e.g.
aromatic hydrocarbon), 2-15 wt % acrylic monomers (e.g.
methylmethacrylate, methacrylic acid and a di- or triacrylate) are
dispersed into an aqueous solution of a protective colloid (e.g.
polyvinyl alcohol). Radical polymerization initiated by a radical
initiator results in the formation of poly(meth)acrylate
microcapsules. Alternatively, an oil phase comprising 5-50 wt % of
a compound I according to the invention, 0-40 wt % water insoluble
organic solvent (e.g. aromatic hydrocarbon), and an isocyanate
monomer (e.g. diphenylmethene-4,4'-diisocyanatae) are dispersed
into an aqueous solution of a protective colloid (e.g. polyvinyl
alcohol). The addition of a polyamine (e.g. hexamethylenediamine)
results in the formation of polyurea microcapsules. The monomers
amount to 1-10 wt %. The wt % relate to the total CS
composition.
ix) Dustable Powders (DP, DS)
[0162] 1-10 wt % of a compound I or VIII, respectively, are ground
finely and mixed intimately with solid carrier (e.g. finely divided
kaolin) ad 100 wt %.
x) Granules (GR, FG)
[0163] 0.5-30 wt % of a compound I or VIII, respectively, is ground
finely and associated with solid carrier (e.g. silicate) ad 100 wt
%. Granulation is achieved by extrusion, spray-drying or fluidized
bed.
xi) Ultra-Low Volume Liquids (UL)
[0164] 1-50 wt % of a compound I or VIII, respectively, are
dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt
%.
[0165] The compositions types i) to xi) may optionally comprise
further auxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt %
anti-freezing agents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt
% colorants.
[0166] The agrochemical compositions generally comprise between
0.01 and 95%, preferably between 0.1 and 90%, and in particular
between 0.5 and 75%, by weight of active substance. The active
substances are employed in a purity of from 90% to 100%, preferably
from 95% to 100% (according to NMR spectrum).
[0167] Solutions for seed treatment (LS), Suspoemulsions (SE),
flowable concentrates (FS), powders for dry treatment (DS),
water-dispersible powders for slurry treatment (WS), water-soluble
powders (SS), emulsions (ES), emulsifiable concentrates (EC) and
gels (GF) are usually employed for the purposes of treatment of
plant propagation materials, particularly seeds. The compositions
in question give, after two-to-tenfold dilution, active substance
concentrations of from 0.01 to 60% by weight, preferably from 0.1
to 40%, in the ready-to-use preparations. Application can be
carried out before or during sowing. Methods for applying compound
I or VIII, respectively, and compositions thereof, respectively, on
to plant propagation material, especially seeds include dressing,
coating, pelleting, dusting, soaking and in-furrow application
methods of the propagation material. Preferably, compound I or
VIII, respectively, or the compositions thereof, respectively, are
applied on to the plant propagation material by a method such that
germination is not induced, e.g. by seed dressing, pelleting,
coating and dusting.
[0168] When employed in plant protection, the amounts of active
substances applied are, depending on the kind of effect desired,
from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha,
more preferably from 0.05 to 0.9 kg per ha, and in particular from
0.1 to 0.75 kg per ha.
[0169] In treatment of plant propagation materials such as seeds,
e.g. by dusting, coating or drenching seed, amounts of active
substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more
preferably from 1 to 100 g and most preferably from 5 to 100 g, per
100 kilogram of plant propagation material (preferably seeds) are
generally required.
[0170] When used in the protection of materials or stored products,
the amount of active substance applied depends on the kind of
application area and on the desired effect. Amounts customarily
applied in the protection of materials are 0.001 g to 2 kg,
preferably 0.005 g to 1 kg, of active substance per cubic meter of
treated material.
[0171] Various types of oils, wetters, adjuvants, fertilizer, or
micronutrients, and further pesticides (e.g. herbicides,
insecticides, fungicides, growth regulators, safeners) may be added
to the active substances or the compositions comprising them as
premix or, if appropriate not until immediately prior to use (tank
mix). These agents can be admixed with the compositions according
to the invention in a weight ratio of 1:100 to 100:1, preferably
1:10 to 10:1.
[0172] The user applies the composition according to the invention
usually from a predosage device, a knapsack sprayer, a spray tank,
a spray plane, or an irrigation system. Usually, the agrochemical
composition is made up with water, buffer, and/or further
auxiliaries to the desired application concentration and the
ready-to-use spray liquor or the agrochemical composition according
to the invention is thus obtained. Usually, 20 to 2000 liters,
preferably 50 to 400 liters, of the ready-to-use spray liquor are
applied per hectare of agricultural useful area.
[0173] According to one embodiment, individual components of the
composition according to the invention such as parts of a kit or
parts of a binary or ternary mixture may be mixed by the user
himself in a spray tank and further auxiliaries may be added, if
appropriate.
[0174] Mixing the compounds I or VIII, respectively, or the
compositions comprising them in the use form as fungicides with
other fungicides results in many cases in an expansion of the
fungicidal spectrum of activity being obtained or in a prevention
of fungicide resistance development. Furthermore, in many cases,
synergistic effects are obtained.
[0175] The following list of active substances, in conjunction with
which the compounds I or VIII, respectively, can be used, is
intended to illustrate the possible combinations but does not limit
them:
A) Respiration Inhibitors
[0176] Inhibitors of complex III at Q.sub.o site (e.g.
strobilurins): azoxystrobin, coumethoxystrobin, coumoxystrobin,
dimoxystrobin, enestroburin, fenaminstrobin,
fenoxystrobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl,
metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin,
pyrametostrobin, pyraoxystrobin, trifloxystrobin,
2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid
methyl ester and
2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-
phenyl)-2-methoxyimino-N-methyl-acetamide, pyribencarb,
triclopyricarb/chlorodincarb, famoxadone, fenamidone; [0177]
inhibitors of complex III at Q.sub.i site: cyazofamid, amisulbrom,
[(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino-
]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,
[(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy).sub.4-methoxy-pyridine-2-c-
arbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,
[(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-c-
arbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate,
[(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyr-
idine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropa-
noate;
(3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]--
6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl
2-methylpropanoate; [0178] inhibitors of complex II (e.g.
carboxamides): benodanil, bixafen, boscalid, carboxin, fenfuram,
fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam,
mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane,
tecloftalam, thifluzamide,
N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyra-
zole-4-carboxamide,
N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4--
carboxamide,
N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-
-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,
3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carbo-
xamide,
3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-
-4-carboxamide,
1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide,
3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4--
carboxamide,
3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-c-
arboxamide,
1,3,5-tri-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide;
[0179] other respiration inhibitors (e.g. complex I, uncouplers):
diflumetorim,
(5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2--
yloxy)-phenyl]-ethyl}-amine; nitrophenyl derivates: binapacryl,
dinobuton, dinocap, fluazinam; ferimzone; organometal compounds:
fentin salts, such as fentin-acetate, fentin chloride or fentin
hydroxide; ametoctradin; and silthiofam;
B) Sterol Biosynthesis Inhibitors (SBI Fungicides)
[0179] [0180] C14 demethylase inhibitors (DMI fungicides):
triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole,
difenoconazole, diniconazole, diniconazole-M, epoxiconazole,
fenbuconazole, fluquinconazole, flusilazole, flutriafol,
hexaconazole, imibenconazole, ipconazole, metconazole,
myclobutanil, oxpoconazole, paclobutrazole, penconazole,
propiconazole, prothioconazole, simeconazole, tebuconazole,
tetraconazole, triadimefon, triadimenol, triticonazole,
uniconazole; imidazoles: imazalil, pefurazoate, prochloraz,
triflumizol; pyrimidines, pyridines and piperazines: fenarimol,
nuarimol, pyrifenox, triforine; [0181] Delta14-reductase
inhibitors: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph,
tridemorph, fenpropidin, piperalin, spiroxamine; [0182] Inhibitors
of 3-keto reductase: fenhexamid;
C) Nucleic Acid Synthesis Inhibitors
[0182] [0183] phenylamides or acyl amino acid fungicides:
benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M
(mefenoxam), ofurace, oxadixyl; [0184] others: hymexazole,
octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine,
5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine,
5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine;
D) Inhibitors of Cell Division and Cytoskeleton
[0184] [0185] tubulin inhibitors, such as benzimidazoles,
thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole,
thiophanate-methyl; triazolopyrimidines:
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]tria-
zolo[1,5-a]pyrimidine [0186] other cell division inhibitors:
diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide,
metrafenone, pyriofenone;
E) Inhibitors of Amino Acid and Protein Synthesis
[0186] [0187] methionine synthesis inhibitors
(anilino-pyrimidines): cyprodinil, mepanipyrim, pyrimethanil;
[0188] protein synthesis inhibitors: blasticidin-S, kasugamycin,
kasugamycin hydrochloridehydrate, mildiomycin, streptomycin,
oxytetracyclin, polyoxine, validamycin A;
F) Signal Transduction Inhibitors
[0188] [0189] MAP/ histidine kinase inhibitors: fluoroimid,
iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil;
[0190] G protein inhibitors: quinoxyfen;
G) Lipid and Membrane Synthesis Inhibitors
[0190] [0191] Phospholipid biosynthesis inhibitors: edifenphos,
iprobenfos, pyrazophos, isoprothiolane; [0192] lipid peroxidation:
dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl,
chloroneb, etridiazole; [0193] phospholipid biosynthesis and cell
wall deposition: dimethomorph, flumorph, mandipropamid, pyrimorph,
benthiavalicarb, iprovalicarb, valifenalate and
N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic
acid-(4-fluorophenyl) ester; [0194] compounds affecting cell
membrane permeability and fatty acides: propamocarb,
propamocarb-hydrochlorid [0195] fatty acid amide hydrolase
inhibitors:
1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1--
piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone;
H) Inhibitors with Multi Site Action [0196] inorganic active
substances: Bordeaux mixture, copper acetate, copper hydroxide,
copper oxychloride, basic copper sulfate, sulfur; [0197] thio- and
dithiocarbamates: ferbam, mancozeb, maneb, metam, metiram,
propineb, thiram, zineb, ziram; [0198] organochlorine compounds
(e.g. phthalimides, sulfamides, chloronitriles): anilazine,
chlorothalonil, captafol, captan, folpet, dichlofluanid,
dichlorophen, flusulfamide, hexachlorobenzene, pentachlorphenole
and its salts, phthalide, tolylfluanid,
N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
[0199] guanidines and others: guanidine, dodine, dodine free base,
guazatine, guazatineacetate, iminoctadine, iminoctadine-triacetate,
iminoctadine-tris(albesilate), dithianon,
2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)tet-
raone;
I) Cell Wall Synthesis Inhibitors
[0199] [0200] inhibitors of glucan synthesis: validamycin, polyoxin
B; melanin synthesis inhibitors: pyroquilon, tricyclazole,
carpropamid, dicyclomet, fenoxanil;
J) Plant Defence Inducers
[0200] [0201] acibenzolar-S-methyl, probenazole, isotianil,
tiadinil, prohexadione-calcium; phosphonates: fosetyl,
fosetyl-aluminum, phosphorous acid and its salts;
K) Unknown Mode of Action
[0201] [0202] bronopol, chinomethionat, cyflufenamid, cymoxanil,
dazomet, debacarb, diclomezine, difenzoquat,
difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover,
flusulfamide, flutianil, methasulfocarb, nitrapyrin,
nitrothal-isopropyl, oxin-copper, proquinazid, tebufloquin,
tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchromen-4-one,
N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methy-
l)-2-phenyl acetamide,
N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-
-methyl formamidine,
N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-
-methyl formamidine,
N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-e-
thyl-N-methyl formamidine,
N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-et-
hyl-N-methyl formamidine,
2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl-
}-thiazole-4-carboxylic acid
methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amide,
2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl-
}-thiazole-4-carboxylic acid
methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide,
1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1--
piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,
methoxy-acetic acid
6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester,
N-Methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl-
]-piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydro-naphthalen-1-yl]-4-thiazoleca-
rboxamide,
3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,
3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine
(pyrisoxazole), N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic
acid amide,
5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazo-
le,
2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop--
2-ynyloxyacetamide; L) Antifungal biocontrol agents, plant
bioactivators: Ampelomyces quisqualie (e.g. AQ 10.RTM. from
Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus (e.g.
AFLAGUARD.RTM. from Syngenta, CH), Aureobasidium pullulans (e.g.
BOTECTOR.RTM. from bio-ferm GmbH, Germany), Bacillus pumilus (e.g.
NRRL Accession No. B-30087 in SONATA.RTM. and BALLAD.RTM. Plus from
AgraQuest Inc., USA), Bacillus subtilis (e.g. isolate NRRL-Nr.
B-21661 in RHAPSODY.RTM., SERENADE.RTM. MAX and SERENADE.RTM. ASO
from AgraQuest Inc., USA), Bacillus subtilise var.
amyloliquefaciens FZB24 (e.g. TAEGRO.RTM. from Novozyme
Biologicals, Inc., USA), Candida oleophila 1-82 (e.g. ASPIRE.RTM.
from Ecogen Inc., USA), Candida saitoana (e.g. BIOCURE.RTM. (in
mixture with lysozyme) and BIOCOAT.RTM. from Micro Flo Company, USA
(BASF SE) and Arysta), Chitosan (e.g. ARMOUR-ZEN from BotriZen
Ltd., NZ), Clonostachys rosea f. catenulata, also named Gliocladium
catenulatum (e.g. isolate J1446: PRESTOP.RTM. from Verdera,
Finland), Coniothyrium minitans (e.g. CONTANS.RTM. from Prophyta,
Germany), Clyphonectria parasitica (e.g. Endothia parasitica from
CNICM, France), Cryptococcus albidus (e.g. YIELD PLUS.RTM. from
Anchor Bio-Technologies, South Africa), Fusarium oxysporum (e.g.
BIOFOX.RTM. from S.I.A.P.A., Italy, FUSACLEAN.RTM. from Natural
Plant Protection, France), Metschnikowia fructicola (e.g.
SHEMER.RTM. from Agrogreen, Israel), Microdochium dimerum (e.g.
ANTIBOT.RTM. from Agrauxine, France), Phlebiopsis gigantea (e.g.
ROTSOP.RTM. from Verdera, Finland), Pseudozyma flocculosa (e.g.
SPORODEX.RTM. from Plant Products Co. Ltd., Canada), Pythium
oligandrum DV74 (e.g. POLYVERSUM.RTM. from Remeslo SSRO,
Biopreparaty, Czech Rep.), Reynoutna sachlinensie (e.g.
REGALIA.RTM. from Marrone Biolnnovations, USA), Talaromyces flavus
V117b (e.g. PROTUS.RTM. from Prophyta, Germany), Trichoderma
asperellum SKT-1 (e.g. ECOHOPE.RTM. from Kumiai Chemical Industry
Co., Ltd., Japan), T. atroviride LC52 (e.g. SENTINEL.RTM. from
Agrimm Technologies Ltd, NZ), T. harzianumT-22 (e.g.
PLANTSHIELD.RTM. der Firma BioWorks Inc., USA), T. harzianum TH 35
(e.g. ROOT PRO.RTM. from Mycontrol Ltd., Israel), T. harzianum T-39
(e.g. TRICHODEX.RTM. and TRICHODERMA 2000.RTM. from Mycontrol Ltd.,
Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride
(e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum
ICC012 and T. viride ICC080 (e.g. REMEDIER.RTM. WP from Isagro
Ricerca, Italy), T. polysporum and T. harzianum (e.g. BINAB.RTM.
from BINAB BioInnovation AB, Sweden), T. stromaticum (e.g.
TRICOVAB.RTM. from C.E.P.L.A.C., Brazil), T. virens GL-21 (e.g.
SOILGARD.RTM. from Certis LLC, USA), T. viride (e.g. TRIECO.RTM.
from Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE.RTM. F from
T. Stanes & Co. Ltd., Indien), T vindeTV1 (e.g. T. viride TV1
from Agribiotec srl, Italy), Ulocladium oudemansii HRU3 (e.g.
BOTRY-ZEN.RTM. from Botry-Zen Ltd, NZ);
M) Growth Regulators
[0203] abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine,
brassinolide, butralin, chlormequat (chlormequat chloride), choline
chloride, cyclanilide, daminozide, dikegulac, dimethipin,
2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol,
fluthiacet, forchlorfenuron, gibberellic acid, inabenfide,
indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat
(mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine,
paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon,
thidiazuron, triapenthenol, tributyl phosphorotrithioate,
2,3,5-tri-iodobenzoic acid, trinexapac-ethyl and uniconazole;
N) Herbicides
[0204] acetamides: acetochlor, alachlor, butachlor, dimethachlor,
dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor,
napropamide, naproanilide, pethoxamid, pretilachlor, propachlor,
thenylchlor; [0205] amino acid derivatives: bilanafos, glyphosate,
glufosinate, sulfosate; [0206] aryloxyphenoxypropionates:
clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop,
metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl; [0207]
Bipyridyls: diquat, paraquat; [0208] (thio)carbamates: asulam,
butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC),
esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb,
pyributicarb, thiobencarb, triallate; [0209] cyclohexanediones:
butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim,
tepraloxydim, tralkoxydim; [0210] dinitroanilines: benfluralin,
ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin;
[0211] diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop,
ethoxyfen, fomesafen, lactofen, oxyfluorfen; [0212]
hydroxybenzonitriles: bomoxynil, dichlobenil, ioxynil; [0213]
imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr,
imazaquin, imazethapyr; [0214] phenoxy acetic acids: clomeprop,
2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA,
MCPA-thioethyl, MCPB, Mecoprop; [0215] pyrazines: chloridazon,
flufenpyr-ethyl, fluthiacet, norflurazon, pyridate; [0216]
pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr,
fluridone, fluroxypyr, picloram, picolinafen, thiazopyr; [0217]
sulfonyl ureas: amidosulfuron, azimsulfuron, bensulfuron,
chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron,
ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron,
foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron,
mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron,
oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron,
rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron,
triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron,
tritosulfuron,
1-((2-chloro-6-propyl-imidazo[1,2-b]pyridazin-3-yOsulfonyl)-3-(4,6-dimeth-
oxy-pyrimidin-2-yl)urea; [0218] triazines: ametryn, atrazine,
cyanazine, dimethametryn, ethiozin, hexazinone, metamitron,
metribuzin, prometryn, simazine, terbuthylazine, terbutryn,
triaziflam; [0219] ureas: chlorotoluron, daimuron, diuron,
fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;
[0220] other acetolactate synthase inhibitors: bispyribac-sodium,
cloransulam-methyl, diclosulam, florasulam, flucarbazone,
flumetsulam, metosulam, ortho-sulfamuron, penoxsulam,
propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid,
pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone,
pyroxsulam; [0221] others: amicarbazone, aminotriazole, anilofos,
beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap,
bentazone, benzobicyclon, bicyclopyrone, bromacil, bromobutide,
butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethyl,
chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide,
dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras,
endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazamide,
flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone,
flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil,
propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic
acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone,
pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotole,
pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione,
sulfentrazone, terbacil, tefuryltrione, tembotrione,
thiencarbazone, topramezone,
(3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-
-2H-pyrimidin-1-yl)-phenoxy]-pyridin-2-yloxy)-acetic acid ethyl
ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidine-4-carboxylic acid
methyl ester,
6-chloro-3-(2-cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol,
4-amino-3-chloro-6-(4-chloro-phenyl)-5-fluoro-pyridine-2-carboxylic
acid,
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)-pyridine-2-carbox-
ylic acid methyl ester, and
4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)-pyridine-2--
carboxylic acid methyl ester.
O) Insecticides
[0221] [0222] organo(thio)phosphates: acephate, azamethiphos,
azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl,
chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate,
disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion,
methamidophos, methidathion, methyl-parathion, mevinphos,
monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate,
phosalone, phosmet, phosphamidon, phorate, phoxim,
pirimiphos-methyl, profenofos, prothiofos, sulprophos,
tetrachlorvinphos, terbufos, triazophos, trichlorfon; [0223]
carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl,
carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb,
methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;
[0224] pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin,
cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin,
zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox,
fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin,
permethrin, prallethrin, pyrethrin I and II, resmethrin,
silafluofen, tau-fluvalinate, tefluthrin, tetramethrin,
tralomethrin, transfluthrin, profluthrin, dimefluthrin; [0225]
insect growth regulators: a) chitin synthesis inhibitors:
benzoylureas: chlorfluazuron, cyramazin, diflubenzuron,
flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,
teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox,
etoxazole, clofentazine; b) ecdysone antagonists: halofenozide,
methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids:
pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis
inhibitors: spirodiclofen, spiromesifen, spirotetramat; [0226]
nicotinic receptor agonists/antagonists compounds: clothianidin,
dinotefuran, flupyradifurone, imidacloprid, thiamethoxam,
nitenpyram, acetamiprid, thiacloprid,
1-2-chloro-thiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1,3,5]triazinane-
; [0227] GABA antagonist compounds: endosulfan, ethiprole,
fipronil, vaniliprole, pyrafluprole, pyriprole,
5-amino-1-(2,6-dichloro-4-methyl-phenyl)-4-sulfinamoyl-1H-pyrazole-3-carb-
othioic acid amide; [0228] macrocyclic lactone insecticides:
abamectin, emamectin, milbemectin, lepimectin, spinosad,
spinetoram; [0229] mitochondrial electron transport inhibitor
(METI) I acaricides: fenazaquin, pyridaben, tebufenpyrad,
tolfenpyrad, flufenerim; [0230] METI II and III compounds:
acequinocyl, fluacyprim, hydramethylnon; [0231] Uncouplers:
chlorfenapyr; [0232] oxidative phosphorylation inhibitors:
cyhexatin, diafenthiuron, fenbutatin oxide, propargite; [0233]
moulting disruptor compounds: cryomazine; [0234] mixed function
oxidase inhibitors: piperonyl butoxide; [0235] sodium channel
blockers: indoxacarb, metaflumizone; [0236] others: benclothiaz,
bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur,
thiocyclam, flubendiamide, chlorantraniliprole, cyazypyr (HGW86),
cyenopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos,
bistrifluron, and pyrifluquinazon.
[0237] The present invention furthermore relates to agrochemical
compositions comprising a mixture of at least one compound I or
VIII, respectively, (component 1) and at least one further active
substance useful for plant protection, e.g. selected from the
groups A) to O) (component 2), in particular one further fungicide,
e.g. one or more fungicide from the groups A) to L), as described
above, and if desired one suitable solvent or solid carrier. Those
mixtures are of particular interest, since many of them at the same
application rate show higher efficiencies against harmful fungi.
Furthermore, combating harmful fungi with a mixture of compounds I
or VIII, respectively, and at least one fungicide from groups A) to
L), as described above, is more efficient than combating those
fungi with individual compounds I or VIII, respectively, or
individual fungicides from groups A) to L). By applying compounds I
or VIII, respectively, together with at least one active substance
from groups A) to O) a synergistic effect can be obtained, i.e.
more then simple addition of the individual effects is obtained
(synergistic mixtures).
[0238] This can be obtained by applying the compounds I or VIII,
respectively, and at least one further active substance
simultaneously, either jointly (e.g. as tank-mix) or seperately, or
in succession, wherein the time interval between the individual
applications is selected to ensure that the active substance
applied first still occurs at the site of action in a sufficient
amount at the time of application of the further active
substance(s). The order of application is not essential for working
of the present invention.
[0239] In binary mixtures, i.e. compositions according to the
invention comprising one compound I or VIII, respectively,
(component 1) and one further active substance (component 2), e.g.
one active substance from groups A) to O), the weight ratio of
component 1 and component 2 generally depends from the properties
of the active substances used, usually it is in the range of from
1:100 to 100:1, regularly in the range of from 1:50 to 50:1,
preferably in the range of from 1:20 to 20:1, more preferably in
the range of from 1:10 to 10:1 and in particular in the range of
from 1:3 to 3:1.
[0240] In ternary mixtures, i.e. compositions according to the
invention comprising one compound I or VIII, respectively,
(component 1) and a first further active substance (component 2)
and a second further active substance (component 3), e.g. two
active substances from groups A) to O), the weight ratio of
component 1 and component 2 depends from the properties of the
active substances used, preferably it is in the range of from 1:50
to 50:1 and particularly in the range of from 1:10 to 10:1, and the
weight ratio of component 1 and component 3 preferably is in the
range of from 1:50 to 50:1 and particularly in the range of from
1:10 to 10:1.
[0241] Preference is also given to mixtures comprising a compound I
or VIII, respectively, (component 1) and at least one active
substance selected from group A) (component 2) and particularly
selected from azoxystrobin, dimoxystrobin, fluoxastrobin,
kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin,
trifloxystrobin; famoxadone, fenamidone; bixafen, boscalid,
fluopyram, fluxapyroxad, isopyrazam, penflufen, penthiopyrad,
sedaxane; ametoctradin, cyazofamid, fluazinam, fentin salts, such
as fentin acetate.
[0242] Preference is given to mixtures comprising a compound of
formula I or VIII, respectively, (component 1) and at least one
active substance selected from group B) (component 2) and
particularly selected from cyproconazole, difenoconazole,
epoxiconazole, fluquinconazole, flusilazole, flutriafol,
metconazole, myclobutanil, penconazole, propiconazole,
prothioconazole, triadimefon, triadimenol, tebuconazole,
tetraconazole, triticonazole, prochloraz, fenarimol, triforine;
dodemorph, fenpropimorph, tridemorph, fenpropidin, spiroxamine;
fenhexamid.
[0243] Preference is given to mixtures comprising a compound of
formula I or VIII, respectively, (component 1) and at least one
active substance selected from group C) (component 2) and
particularly selected from metalaxyl, (metalaxyl-M) mefenoxam,
ofurace.
[0244] Preference is given to mixtures comprising a compound of
formula I or VIII, respectively, (component 1) and at least one
active substance selected from group D) (component 2) and
particularly selected from benomyl, carbendazim,
thiophanate-methyl, ethaboxam, fluopicolide, zoxamide, metrafenone,
pyriofenone.
[0245] Preference is also given to mixtures comprising a compound I
or VIII, respectively, (component 1) and at least one active
substance selected from group E) (component 2) and particularly
selected from cyprodinil, mepanipyrim, pyrimethanil.
[0246] Preference is also given to mixtures comprising a compound I
or VIII, respectively, (component 1) and at least one active
substance selected from group F) (component 2) and particularly
selected from iprodione, fludioxonil, vinclozolin, quinoxyfen.
[0247] Preference is also given to mixtures comprising a compound I
or VIII, respectively, (component 1) and at least one active
substance selected from group G) (component 2) and particularly
selected from dimethomorph, flumorph, iprovalicarb,
benthiavalicarb, mandipropamid, propamocarb.
[0248] Preference is also given to mixtures comprising a compound I
or VIII, respectively, (component 1) and at least one active
substance selected from group H) (component 2) and particularly
selected from copper acetate, copper hydroxide, copper oxychloride,
copper sulfate, sulfur, mancozeb, metiram, propineb, thiram,
captafol, folpet, chlorothaIonil, dichlofluanid, dithianon.
[0249] Preference is also given to mixtures comprising a compound I
or VIII, respectively, (component 1) and at least one active
substance selected from group I) (component 2) and particularly
selected from carpropamid and fenoxanil.
[0250] Preference is also given to mixtures comprising a compound I
or VIII, respectively, (component 1) and at least one active
substance selected from group J) (component 2) and particularly
selected from acibenzolar-S-methyl, probenazole, tiadinil, fosetyl,
fosetyl-aluminium, H.sub.3P03 and salts thereof.
[0251] Preference is also given to mixtures comprising a compound I
or VIII, respectively, (component 1) and at least one active
substance selected from group K) (component 2) and particularly
selected from cymoxanil, proquinazid and
N-methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piper-
idin-4-yl}-N-[(1R)-1,2,3,4-tetrahydro-naphthalen-1-yl]-4-thiazolecarboxami-
de.
[0252] Preference is also given to mixtures comprising a compound I
or VIII, respectively, (component 1) and at least one active
substance selected from group L) (component 2) and particularly
selected from Bacillus subtilis strain NRRL No. B-21661, Bacillus
pumllus strain NRRL No. B-30087 and Ulocladium oudemansii.
[0253] Accordingly, the present invention furthermore relates to
compositions comprising one compound I or VIII, respectively,
(component 1) and one further active substance (component 2), which
further active substance is selected from the column "Component 2"
of the lines B-1 to B-372 of Table B.
[0254] A further embodiment relates to the compositions B-1 to
B-372 listed in Table B, where a row of Table B corresponds in each
case to a fungicidal composition comprising one of the in the
present specification individualized compounds of formula I
(component 1) and the respective further active substance from
groups A) to O) (component 2) stated in the row in question.
Preferably, the compositions described comprise the active
substances in synergistically effective amounts.
TABLE-US-00006 TABLE B Composition comprising one indiviualized
compound I and one further active substance from groups A) to O)
Mixture Component 1 Component 2 B-1 one individualized compound I
Azoxystrobin B-2 one individualized compound I Coumethoxystrobin
B-3 one individualized compound I Coumoxystrobin B-4 one
individualized compound I Dimoxystrobin B-5 one individualized
compound I Enestroburin B-6 one individualized compound I
Fenaminstrobin B-7 one individualized compound I
Fenoxystrobin/Flufenoxystrobin B-8 one individualized compound I
Fluoxastrobin B-9 one individualized compound I Kresoxim-methyl
B-10 one individualized compound I Metominostrobin B-11 one
individualized compound I Orysastrobin B-12 one individualized
compound I Picoxystrobin B-13 one individualized compound I
Pyraclostrobin B-14 one individualized compound I Pyrametostrobin
B-15 one individualized compound I Pyraoxystrobin B-16 one
individualized compound I Pyribencarb B-17 one individualized
compound I Trifloxystrobin B-18 one individualized compound I
Triclopyricarb/Chlorodincarb B-19 one individualized compound I
2-[2-(2,5-dimethyl-phenoxymethyl)- phenyl]-3-methoxy-acrylic acid
methyl ester B-20 one individualized compound I
2-(2-(3-(2,6-dichlorophenyl)-1-methyl-
allylideneaminooxymethyl)-phenyl)-
2-methoxyimino-N-methyl-acetamide B-21 one individualized compound
I Benalaxyl B-22 one individualized compound I Benalaxyl-M B-23 one
individualized compound I Benodanil B-24 one individualized
compound I Bixafen B-25 one individualized compound I Boscalid B-26
one individualized compound I Carboxin B-27 one individualized
compound I Fenfuram B-28 one individualized compound I Fenhexamid
B-29 one individualized compound I Flutolanil B-30 one
individualized compound I Fluxapyroxad B-31 one individualized
compound I Furametpyr B-32 one individualized compound I Isopyrazam
B-33 one individualized compound I Isotianil B-34 one
individualized compound I Kiralaxyl B-35 one individualized
compound I Mepronil B-36 one individualized compound I Metalaxyl
B-37 one individualized compound I Metalaxyl-M B-38 one
individualized compound I Ofurace B-39 one individualized compound
I Oxadixyl B-40 one individualized compound I Oxycarboxin B-41 one
individualized compound I Penflufen B-42 one individualized
compound I Penthiopyrad B-43 one individualized compound I Sedaxane
B-44 one individualized compound I Tecloftalam B-45 one
individualized compound I Thifluzamide B-46 one individualized
compound I Tiadinil B-47 one individualized compound I
2-Amino-4-methyl-thiazole-5-carboxylic acid anilide B-48 one
individualized compound I N-(4'-trifluoromethylthiobiphenyl-2-yl)-
3-difluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide B-49 one
individualized compound I N-(2-(1,3,3-trimethyl-butyl)-phenyl)-
1,3-dimethyl-5-fluoro-1H-pyrazole- 4-carboxamide B-50 one
individualized compound I N-[9-(dichloromethylene)-1,2,3,4-tetra-
hydro-1,4-methanonaphthalen-5-yl]-
3-(difluoromethyl)-1-methyl-1H-pyrazole- 4-carboxamide B-51 one
individualized compound I Dimethomorph B-52 one individualized
compound I Flumorph B-53 one individualized compound I Pyrimorph
B-54 one individualized compound I Flumetover B-55 one
individualized compound I Fluopicolide B-56 one individualized
compound I Fluopyram B-57 one individualized compound I Zoxamide
B-58 one individualized compound I Carpropamid B-59 one
individualized compound I Diclocymet B-60 one individualized
compound I Mandipropamid B-61 one individualized compound I
Oxytetracyclin B-62 one individualized compound I Silthiofam B-63
one individualized compound I N-(6-methoxy-pyridin-3-yl)
cyclopropanecarboxylic acid amide B-64 one individualized compound
I Azaconazole B-65 one individualized compound I Bitertanol B-66
one individualized compound I Bromuconazole B-67 one individualized
compound I Cyproconazole B-68 one individualized compound I
Difenoconazole B-69 one individualized compound I Diniconazole B-70
one individualized compound I Diniconazole-M B-71 one
individualized compound I Epoxiconazole B-72 one individualized
compound I Fenbuconazole B-73 one individualized compound I
Fluquinconazole B-74 one individualized compound I Flusilazole B-75
one individualized compound I Flutriafol B-76 one individualized
compound I Hexaconazol B-77 one individualized compound I
Imibenconazole B-78 one individualized compound I Ipconazole B-79
one individualized compound I Metconazole B-80 one individualized
compound I Myclobutanil B-81 one individualized compound I
Oxpoconazol B-82 one individualized compound I Paclobutrazol B-83
one individualized compound I Penconazole B-84 one individualized
compound I Propiconazole B-85 one individualized compound I
Prothioconazole B-86 one individualized compound I Simeconazole
B-87 one individualized compound I Tebuconazole B-88 one
individualized compound I Tetraconazole B-89 one individualized
compound I Triadimefon B-90 one individualized compound I
Triadimenol B-91 one individualized compound I Triticonazole B-92
one individualized compound I Uniconazole B-93 one individualized
compound I Cyazofamid B-94 one individualized compound I Imazalil
B-95 one individualized compound I Imazalil-sulfate B-96 one
individualized compound I Pefurazoate B-97 one individualized
compound I Prochloraz B-98 one individualized compound I
Triflumizole B-99 one individualized compound I Benomyl B-100 one
individualized compound I Carbendazim B-101 one individualized
compound I Fuberidazole B-102 one individualized compound I
Thiabendazole B-103 one individualized compound I Ethaboxam B-104
one individualized compound I Etridiazole B-105 one individualized
compound I Hymexazole B-106 one individualized compound I
2-(4-Chloro-phenyl)-N-[4-(3,4-dimethoxy-
phenyl)-isoxazol-5-yl]-2-prop-2-yn- yloxy-acetamide B-107 one
individualized compound I Fluazinam B-108 one individualized
compound I Pyrifenox B-109 one individualized compound I
3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin- 3-yl]-pyridine
(Pyrisoxazole) B-110 one individualized compound I
3-[5-(4-Methyl-phenyl)-2,3-dimethyl- isoxazolidin-3-yl]-pyridine
B-111 one individualized compound I Bupirimate B-112 one
individualized compound I Cyprodinil B-113 one individualized
compound I 5-Fluorocytosine B-114 one individualized compound I
5-Fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine B-115 one
individualized compound I 5-Fluoro-2-(4-fluorophenylmethoxy)-
pyrimidin-4-amine B-116 one individualized compound I Diflumetorim
B-117 one individualized compound I
(5,8-Difluoroquinazolin-4-yl)-{2-[2-fluoro-
4-(4-trifluoromethylpyridin-2-yloxy)- phenyl]-ethyl}-amine B-118
one individualized compound I Fenarimol B-119 one individualized
compound I Ferimzone B-120 one individualized compound I
Mepanipyrim B-121 one individualized compound I Nitrapyrin B-122
one individualized compound I Nuarimol B-123 one individualized
compound I Pyrimethanil B-124 one individualized compound I
Triforine B-125 one individualized compound I Fenpiclonil B-126 one
individualized compound I Fludioxonil B-127 one individualized
compound I Aldimorph B-128 one individualized compound I Dodemorph
B-129 one individualized compound I Dodemorph-acetate B-130 one
individualized compound I Fenpropimorph B-131 one individualized
compound I Tridemorph B-132 one individualized compound I
Fenpropidin B-133 one individualized compound I Fluoroimid B-134
one individualized compound I Iprodione B-135 one individualized
compound I Procymidone B-136 one individualized compound I
Vinclozolin B-137 one individualized compound I Famoxadone B-138
one individualized compound I Fenamidone B-139 one individualized
compound I Flutianil B-140 one individualized compound I
Octhilinone B-141 one individualized compound I Probenazole B-142
one individualized compound I Fenpyrazamine B-143 one
individualized compound I Acibenzolar-S-methyl B-144 one
individualized compound I Ametoctradin B-145 one individualized
compound I Amisulbrom B-146 one individualized compound I
[(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutyryloxymethoxy-
4-methoxypyridine- 2-carbonyl)amino]-6-methyl-4,9-dioxo-
[1,5]dioxonan-7-yl] 2-methylpropanoate B-147 one individualized
compound I [(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-
4-methoxy-pyridine-2-carbonyl)amino]-
6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate B-148 one
individualized compound I
[(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)- 4-methoxy-pyridine-
2-carbonyl]amino]-6-methyl-4,9-dioxo- 1,5-dioxonan-7-yl]
2-methylpropanoate B-149 one individualized compound I
[(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-
4-methoxy-pyridine- 2-carbonyl)amino]-6-methyl-4,9-dioxo-
1,5-dioxonan-7-yl] 2-methylpropanoate B-150 one individualized
compound I [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol-
5-ylmethoxy)-4-methoxy-pyridine- 2-carbonyl]amino]-6-methyl-4,9-di-
oxo-1,5-dioxonan-7-yl] 2-methyl- propanoate B-151 one
individualized compound I Anilazin B-152 one individualized
compound I Blasticidin-S B-153 one individualized compound I
Captafol B-154 one individualized compound I Captan B-155 one
individualized compound I Chinomethionat B-156 one individualized
compound I Dazomet B-157 one individualized compound I Debacarb
B-158 one individualized compound I Diclomezine B-159 one
individualized compound I Difenzoquat, B-160 one individualized
compound I Difenzoquat-methylsulfate B-161 one individualized
compound I Fenoxanil B-162 one individualized compound I Folpet
B-163 one individualized compound I Oxolinsaure B-164 one
individualized compound I Piperalin B-165 one individualized
compound I Proquinazid B-166 one individualized compound I
Pyroquilon B-167 one individualized compound I Quinoxyfen B-168 one
individualized compound I Triazoxid B-169 one individualized
compound I Tricyclazole B-170 one individualized compound I
2-Butoxy-6-iodo-3-propyl-chromen-4- one B-171 one individualized
compound I 5-Chloro-1-(4,6-dimethoxy-pyrimidin-2-
yl)-2-methyl-1H-benzoimidazole B-172 one individualized compound I
5-Chloro-7-(4-methyl-piperidin-1-yl)-
6-(2,4,6-trifluoro-phenyl)-[1,2,4]tri- azolo[1,5-a]pyrimidine B-173
one individualized compound I Ferbam B-174 one individualized
compound I Mancozeb B-175 one individualized compound I Maneb B-176
one individualized compound I Metam B-177 one individualized
compound I Methasulphocarb B-178 one individualized compound I
Metiram B-179 one individualized compound I Propineb B-180 one
individualized compound I Thiram B-181 one individualized compound
I Zineb B-182 one individualized compound I Ziram B-183 one
individualized compound I Diethofencarb B-184 one individualized
compound I Benthiavalicarb B-185 one individualized compound I
Iprovalicarb B-186 one individualized compound I Propamocarb B-187
one individualized compound I Propamocarb hydrochlorid B-188 one
individualized compound I Valifenalate B-189 one individualized
compound I N-(1-(1-(4-cyanophenyl)ethanesulfonyl)-
but-2-yl) carbamic acid-(4-fluoro- phenyl) ester B-190 one
individualized compound I Dodine B-191 one individualized compound
I Dodine free base B-192 one individualized compound I Guazatine
B-193 one individualized compound I Guazatine-acetate B-194 one
individualized compound I Iminoctadine B-195 one individualized
compound I Iminoctadine-triacetate B-196 one individualized
compound I Iminoctadine-tris(albesilate) B-197 one individualized
compound I Kasugamycin B-198 one individualized compound I
Kasugamycin-hydrochloride-hydrate B-199 one individualized compound
I Polyoxine B-200 one individualized compound I Streptomycin B-201
one individualized compound I Validamycin A B-202 one
individualized compound I Binapacryl B-203 one individualized
compound I Dicloran B-204 one individualized compound I Dinobuton
B-205 one individualized compound I Dinocap B-206 one
individualized compound I Nitrothal-isopropyl B-207 one
individualized compound I Tecnazen B-208 one individualized
compound I Fentin salts B-209 one individualized compound I
Dithianon B-210 one individualized compound I Isoprothiolane B-211
one individualized compound I Edifenphos B-212 one individualized
compound I Fosetyl, Fosetyl-aluminium B-213 one individualized
compound I Iprobenfos B-214 one individualized compound I
Phosphorous acid (H.sub.3PO.sub.3) and derivatives B-215 one
individualized compound I Pyrazophos B-216 one individualized
compound I Tolclofos-methyl B-217 one individualized compound I
Chlorothalonil B-218 one individualized compound I Dichlofluanid
B-219 one individualized compound I Dichlorophen B-220 one
individualized compound I Flusulfamide B-221 one individualized
compound I Hexachlorbenzene B-222 one individualized compound I
Pencycuron B-223 one individualized compound I Pentachlorophenol
and salts B-224 one individualized compound I Phthalide B-225 one
individualized compound I Quintozene B-226 one individualized
compound I Thiophanate Methyl B-227 one individualized compound I
Tolylfluanid B-228 one individualized compound I
N-(4-chloro-2-nitro-phenyl)-N-ethyl- 4-methyl-benzenesulfonamide
B-229 one individualized compound I Bordeaux mixture B-230 one
individualized compound I Copper acetate B-231 one individualized
compound I Copper hydroxide B-232 one individualized compound I
Copper oxychloride B-233 one individualized compound I basic Copper
sulfate B-234 one individualized compound I Sulfur B-235 one
individualized compound I Biphenyl B-236 one individualized
compound I Bronopol B-237 one individualized compound I
Cyflufenamid B-238 one individualized compound I Cymoxanil B-239
one individualized compound I Diphenylamin B-240 one individualized
compound I Metrafenone B-241 one individualized compound I
Pyriofenone B-242 one individualized compound I Mildiomycin B-243
one individualized compound I Oxin-copper B-244 one individualized
compound I Prohexadione calcium B-245 one individualized compound I
Spiroxamine B-246 one individualized compound I Tebufloquin B-247
one individualized compound I Tolylfluanid B-248 one individualized
compound I N-(Cyclopropylmethoxyimino-(6-
difluoromethoxy-2,3-difluoro-phenyl)- methyl)-2-phenyl acetamide
B-249 one individualized compound I
N'-(4-(4-chloro-3-trifluoromethyl-
phenoxy)-2,5-dimethyl-phenyl)-N-ethyl- N-methyl formamidine B-250
one individualized compound I N'-(4-(4-fluoro-3-trifluoromethyl-
phenoxy)-2,5-dimethyl-phenyl)-N-ethyl- N-methyl formamidine B-251
one individualized compound I
N'-(2-methyl-5-trifluoromethyl-4-(3-tri-
methylsilanyl-propoxy)-phenyl)-N-ethyl- N-methyl formamidine B-252
one individualized compound I
N'-(5-difluoromethyl-2-methyl-4-(3-tri-
methylsilanyl-propoxy)-phenyl)-N-ethyl- N-methyl formamidine B-253
one individualized compound I 2-{1-[2-(5-Methyl-3-trifluoromethyl-
pyrazole-1-yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid
methyl- (1,2,3,4-tetrahydro-naphthalen-1-yl)- amide B-254 one
individualized compound I 2-{1-[2-(5-Methyl-3-trifluoromethyl-
pyrazole-1-yl)-acetyl]-piperidin-4-yl}- thiazole-4-carboxylic acid
methyl-(R)- 1,2,3,4-tetrahydro-naphthalen-1-yl- amide B-255 one
individualized compound I 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-di-
hydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-
2-[5-methyl-3-(trifluoro- methyl)-1H-pyrazol-1-yl]ethanone B-256
one individualized compound I Methoxy-acetic acid 6-tert-butyl-8-
fluoro-2,3-dimethyl-quinolin-4-yl ester B-257 one individualized
compound I N-Methyl-2-{1-[(5-methyl-3-trifluoro-
methyl-1H-pyrazol-1-yl)-acetyl]-piperidin-
4-yl}-N-[(1R)-1,2,3,4-tetrahydro-
naphthalen-1-yl]-4-thiazolecarboxamide B-258 one individualized
compound I Bacillus subtilis NRRL No. B-21661 B-259 one
individualized compound I Bacillus pumilus NRRL No. B-30087 B-260
one individualized compound I Ulocladium oudemansii B-261 one
individualized compound I Carbaryl B-262 one individualized
compound I Carbofuran B-263 one individualized compound I
Carbosulfan B-264 one individualized compound I Methomylthiodicarb
B-265 one individualized compound I Bifenthrin B-266 one
individualized compound I Cyfluthrin B-267 one individualized
compound I Cypermethrin B-268 one individualized compound I
alpha-Cypermethrin B-269 one individualized compound I
zeta-Cypermethrin B-270 one individualized compound I Deltamethrin
B-271 one individualized compound I Esfenvalerate B-272 one
individualized compound I Lambda-cyhalothrin B-273 one
individualized compound I Permethrin B-274 one individualized
compound I Tefluthrin B-275 one individualized compound I
Diflubenzuron B-276 one individualized compound I Flufenoxuron
B-277 one individualized compound I Lufenuron B-278 one
individualized compound I Teflubenzuron B-279 one individualized
compound I Spirotetramate B-280 one individualized compound I
Clothianidin B-281 one individualized compound I Dinotefuran B-282
one individualized compound I Imidacloprid B-283 one individualized
compound I Thiamethoxam B-284 one individualized compound I
Flupyradifurone B-285 one individualized compound I Acetamiprid
B-286 one individualized compound I Thiacloprid B-287 one
individualized compound I Endosulfan B-288 one individualized
compound I Fipronil B-289 one individualized compound I Abamectin
B-290 one individualized compound I Emamectin B-291 one
individualized compound I Spinosad B-292 one individualized
compound I Spinetoram B-293 one individualized compound I
Hydramethylnon B-294 one individualized compound I Chlorfenapyr
B-295 one individualized compound I Fenbutatin oxide B-296 one
individualized compound I Indoxacarb B-297 one individualized
compound I Metaflumizone B-298 one individualized compound I
Flonicamid B-299 one individualized compound I Lubendiamide B-300
one individualized compound I Chlorantraniliprole B-301 one
individualized compound I Cyazypyr (HGW86) B-302 one individualized
compound I Cyflumetofen B-303 one individualized compound I
Acetochlor B-304 one individualized compound I Dimethenamid B-305
one individualized compound I metolachlor B-306 one individualized
compound I Metazachlor B-307 one individualized compound I
Glyphosate B-308 one individualized compound I Glufosinate B-309
one individualized compound I Sulfosate B-310 one individualized
compound I Clodinafop B-311 one individualized compound I
Fenoxaprop B-312 one individualized compound I Fluazifop B-313 one
individualized compound I Haloxyfop B-314 one individualized
compound I Paraquat B-315 one individualized compound I
Phenmedipham B-316 one individualized compound I Clethodim B-317
one individualized compound I Cycloxydim B-318 one individualized
compound I Profoxydim B-319 one individualized compound I
Sethoxydim B-320 one individualized compound I Tepraloxydim B-321
one individualized compound I Pendimethalin B-322 one
individualized compound I Prodiamine B-323 one individualized
compound I Trifluralin B-324 one individualized compound I
Acifluorfen B-325 one individualized compound I Bromoxynil B-326
one individualized compound I Imazamethabenz B-327 one
individualized compound I Imazamox B-328 one individualized
compound I Imazapic B-329 one individualized compound I Imazapyr
B-330 one individualized compound I Imazaquin B-331 one
individualized compound I Imazethapyr B-332 one individualized
compound I 2,4-Dichlorophenoxyacetic acid (2,4-D) B-333 one
individualized compound I Chloridazon B-334 one individualized
compound I Clopyralid B-335 one individualized compound I
Fluroxypyr B-336 one individualized compound I Picloram B-337 one
individualized compound I Picolinafen B-338 one individualized
compound I Bensulfuron B-339 one individualized compound I
Chlorimuron-ethyl B-340 one individualized compound I
Cyclosulfamuron B-341 one individualized compound I Iodosulfuron
B-342 one individualized compound I Mesosulfuron B-343 one
individualized compound I Metsulfuron-methyl B-344 one
individualized compound I Nicosulfuron B-345 one individualized
compound I Rimsulfuron B-346 one individualized compound I
Triflusulfuron B-347 one individualized compound I Atrazine B-348
one individualized compound I Hexazinone B-349 one individualized
compound I Diuron B-350 one individualized compound I Florasulam
B-351 one individualized compound I Pyroxasulfone B-352 one
individualized compound I Bentazone B-353 one individualized
compound I Cinidon-ethyl B-354 one individualized compound I
Cinmethylin B-355 one individualized compound I Dicamba B-356 one
individualized compound I Diflufenzopyr B-357 one individualized
compound I Quinclorac B-358 one individualized compound I Quinmerac
B-359 one individualized compound I Mesotrione B-360 one
individualized compound I Saflufenacil B-361 one individualized
compound I Topramezone B-362 one individualized compound I
(3S,6S,7R,8R)-3-[[(3-hydroxy-4-
methoxy-2-pyridinyl)carbonyl]amino]-
6-methyl-4,9-dioxo-8-(phenylmethyl)- 1,5-dioxonan-7-yl
2-methylpropanoate B-363 one individualized compound I
[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-
difluorophenyl)-oxiranylmethyl]-5-thio- cyanato-1H-[1,2,4]triazole,
B-364 one individualized compound I
2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-
(2,4-difluorophenyl)-oxiranylmethyl]- 2H-[1,2,4]triazole-3-thiol
B-365 one individualized compound I
1-[4-[4-[5-(2,6-difluorophenyl)-4,5-
dihydro-3-isoxazolyl]-2-thiazolyl]-1-
piperidinyl]-2-[5-methyl-3-(trifluoro-
methyl)-1H-pyrazol-1-yl]ethanone B-366 one individualized compound
I 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-
c:5,6-c']dipyrrole-1,3,5,7(2H,6H)- tetraone B-367 one
individualized compound I 3-(difluoromethyl)-1-methyl-N-(1,1,3-
trimethylindan-4-yl)pyrazole-4- carboxamide B-368 one
individualized compound I 3-(trifluoromethyl)-1-methyl-N-(1,1,3-
trimethylindan-4-yl)pyrazole-4- carboxamide B-369 one
individualized compound I 1,3-dimethyl-N-(1,1,3-trimethylindan-4-
yl)pyrazole-4-carboxamide B-370 one individualized compound I
3-(trifluorometh-yl)-1,5-dimethyl-N-
(1,1,3-trimethylindan-4-yl)pyrazole-4- carboxamide B-371 one
individualized compound I 3-(difluoro-methyl)-1,5-dimethyl-N-
(1,1,3-trimethylindan-4-yl)pyrazole-4- carboxamide B-372 one
individualized compound I 1,3,5-tri-methyl-N-(1,1,3-trimethylindan-
4-yl)pyrazole-4-carboxamide
[0255] A further embodiment relates to the compositions B2-1 to
B2-372 listed in Table B2, where a row of Table B2 corresponds in
each case to a fungicidal composition comprising one of the in the
present specification individualized compounds of formula VIII
(component 1) and the respective further active substance from
groups A) to O) (component 2) stated in the row in question.
Preferably, the compositions described comprise the active
substances in synergistically effective amounts.
Table B2:
[0256] Composition comprising one individualized compound VIII and
one further active substance from groups A) to O). This table
corresponds to table B, wherein in the first column the number/name
of the individualized mixture is named "B2- . . . " instead of "B-
. . . " and in the second column, it says in each line "one
individualized compound VIII" instead of "one individualized
compound I".
[0257] The active substances referred to as component 2, their
preparation and their activity against harmful fungi is known (cf.:
http://www.alanwood.net/pesticides/); these substances are
commercially available. The compounds described by IUPAC
nomenclature, their preparation and their fungicidal activity are
also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141
317; EP-A 152 031; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A
428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201
648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE
102005009458; U.S. Pat. No. 3,296,272; U.S. Pat. No. 3,325,503; WO
98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO
00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO
02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO
03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO
04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO
05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO
07/82098; WO 07/90624, WO 11/028657).
[0258] The mixtures of active substances can be prepared as
compositions comprising besides the active ingridients at least one
inert ingredient by usual means, e.g. by the means given for the
compositions of compounds I.
[0259] Concerning usual ingredients of such compositions reference
is made to the explanations given for the compositions containing
compounds I.
[0260] The mixtures of active substances according to the present
invention are suitable as fungicides, as are the compounds of
formula I. They are distinguished by an outstanding effectiveness
against a broad spectrum of phytopathogenic fungi, especially from
the classes of the Ascomycetes, Basidiomycetes, Deuteromycetes and
Peronosporomycetes (syn. Oomycetes). In addition, it is refered to
the explanations regarding the fungicidal activity of the compounds
and the compositions containing compounds I, respectively.
I. SYNTHESIS EXAMPLES
[0261] With due modification of the starting compounds, the
procedures shown in the synthesis examples below were used to
obtain further compounds I. The resulting compounds, together with
physical data, are listed in Table I below.
[0262] The compounds I listed in Table I have been prepared in an
analogous manner.
TABLE-US-00007 TABLE I HPLC* ex.-no. X.sup.1 X.sup.2 R.sup.1
R.sup.2 R.sub.t (min) I-1 Cl Cl C.ident.CH CH.sub.3 1.24 I-2 Cl Cl
C.ident.CH C.sub.2H.sub.5 1.30 I-3 Cl Cl C.ident.CH
CH.sub.2C.ident.CH 1.24 I-4 Cl Cl C.ident.CH CH.sub.2C.sub.6H.sub.5
1.38 I-5 Cl Cl C.ident.CH CH.sub.2CH.sub.2CH.sub.3 1.35 I-6 Cl Cl
(E)CH.dbd.CHC.sub.6H.sub.5 CH.sub.2C.ident.CH 1.39 I-7 Cl Cl
CH.dbd.CH.sub.2 CH.sub.3 1.27 I-8 Cl Cl CH.dbd.CH.sub.2
CH.sub.2CH.dbd.CH.sub.2 1.35 I-9 Cl Cl CH.dbd.CH.sub.2
CH.sub.2C.ident.CH 1.28 I-10 Cl Cl C.ident.CCH.sub.3 CH.sub.3 1.28
I-11 Cl Cl C.ident.CCH.sub.3 C.sub.2H.sub.5 1.35 I-12 Cl Cl
C.ident.CCH.sub.3 CH.sub.2CH.dbd.CH.sub.2 1.36 I-13 Cl Cl
C.ident.CCH.sub.3 CH.sub.2C.ident.CH 1.29 I-14 Cl Cl
CH.sub.2C(Cl).dbd.CHCl CH.sub.3 1.09 I-15 Cl Cl CH.sub.2C.ident.CH
CH.sub.2C.ident.CH 1.24 I-16 Cl Cl C.ident.CCH.sub.3
CH.sub.2C(Cl).dbd.CHCl 1.42 *HPLC methode Data: Mobile Phase: A:
Water + 0.1% TFA, B: acetonitrile; Gradient: 5% B to 100% B in 1.5
min; Temperature: 60.degree. C.; MS method: ESI positive; mass area
(m/z); 10-700; Flow: 0.8 ml/min to 1.0 ml/min in 1.5 min; Column:
Kinetex XB C18 1.7.mu. 50 .times. 2.1 mm; Aparatus: Shimadzu Nexera
LC-30 LCMS-2020
EXAMPLE 1
Synthesis of
1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-but-3-enyl]-1,2,4-tri-
azole (compound 1-7)
Step 1: 2-bromo-1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone
[0263] 1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone (1000 g) was
dissolved in MTBE (5000 mL) and a solution of bromine (563 g) in
glacial acetic acid (400 mL) was added dropwise at room
temperature. After completion of the addition the mixture was
stirred for 1 h at room temperature and the pH was adjusted to 7-8
by addition of 10% NaOH solution. The organic layer was separated,
extracted twice with MTBE and the combined organic phases were
washed with sat. NaHCO3 solution (1.times.) and brine (2.times.).
The solvent was evaporated and the crude product was used directly
in the next step.
Step 2:
1-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-(1,2,4-triazol-1-yl)ethan-
one
[0264] 1,2,4-Triazole (249 g) was added carefully (small portions)
to a mixture of sodium hydride (85 g) in THF (6000 mL). After 30
minutes a solution of
2-bromo-1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone (1322 g) in
THF (500 mL) was slowly added and the mixture was stirred for 150
min. The pH was adjusted to 7 with dil. hydrochloric acid whereupon
water was added (3000 mL). The precipitate was filtered off and
washed with MTBE. The organic phase was then concentrated and the
resulting solid was filtered off to yield the desired material
(1008 g).
Step
3.2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)but-3--
en-2-ol
[0265] A solution of
1-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-(1,2,4-triazol-1-yl)ethanone
(8 g) in dichloromethane (250 mL) was added slowly to a suspension
of magnesiumbromide etherate (14 g) in dichloromethane (130 mL).
The resulting mixture was stirred at room temperature for 1 h
whereupon a solution of vinyl magnesium chloride in diethyl ether
(1 M, 46 mL) was added dropwise at -15.degree. C. The mixture was
stirred for 2 h and allowed to thaw. 15% NH4Cl solution (200 mL)
was added carefully under cooling. The phases were separated and
the organic layer was subsequently washed with water and brine and
dried. The solvent was evaporated under reduced pressure. The crude
product was crystallized from MTBE to obtain 1.4 g of the desired
compound.
Step 4:
1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-but-3-enyl]-1,-
2,4-triazole
[0266]
2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)but-3--
en-2-ol (0.4 g) was dissolved in THF (10 mL) and sodium hydride
(0.03 g) was added. The mixture was stirred for 30 min at room
temperature and methyl iodide (0.08 mL) was added. The mixture was
then heated for 10 h to reflux. Brine and dichloro methane were
added, the organic phase was dried and evaporated to obtain the
crude product. This was purified by column chromatography to obtain
0.04 g of the desired compound.
II. Biology
1) Green House
[0267] The spray solutions were prepared in several steps:
[0268] The stock solution were prepared: a mixture of acetone
and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol,
which is based on ethoxylated alkylphenoles, in a relation (volume)
solvent-emulsifier of 99 to 1 was added to 25 mg of the compound to
give a total of 5 ml. Water was then added to total volume of 100
ml.
[0269] This stock solution was diluted with the described
solvent-emulsifier-water mixture to the given concentration.
G1. Preventative Control of Leaf Blotch on Wheat Caused by Septoria
tritici (Septtr P1)
[0270] Leaves of pot-grown wheat seedling were sprayed to run-off
with an aqueous suspension of the active compound or their mixture,
prepared as described. The plants were allowed to air-dry. The next
day the plants were inoculated with an aqueous spore suspension of
Septoria tritici. Then the trial plants were immediately
transferred to a humid chamber at 18-22.degree. C. and a relative
humidity close to 100%. After 4 days the plants were transferred to
a chamber with 18-22.degree. C. and a relative humidity close to
70%. After 4 weeks the extent of fungal attack on the leaves was
visually assessed as % diseased leaf area. In this test, the plants
which had been treated with 300 ppm of the active substance from
examples I-1, I-7, I-8, I-11, I-12, I-13 and 1-15, respectively,
showed an infection of equal to or less 1% whereas the untreated
plants were 90% infected.
G2. Preventative Fungicidal Control of Early Blight on Tomatoes
(Alternaria solani) (Alteso P1) Young seedlings of tomato plants
were grown in pots. These plants were sprayed to run-off with an
aqueous suspension, containing the concentration of active
ingredient or mixture mentioned in the table below. The next day,
the treated plants were inoculated with an aqueous suspension of
Alternaria solani Then the trial plants were immediately
transferred to a humid chamber. After 5 days at 18 to 20.degree. C.
and a relative humidity close to 100%, the extent of fungal attack
on the leaves was visually assessed as % diseased leaf area. In
this test, the plants which had been treated with 300 ppm of the
active substance from examples I-1, I-2, I-3, I-5, I-7, I-8, I-9,
I-10, I-11, I-12, I-13 and 1-15, respectively, showed an infection
of equal to or less than 7% whereas the untreated plants were 90%
infected. G3. Preventative Control of Brown Rust on Wheat Caused by
Puccinia recondite (Puccrt P1)
[0271] The first two developed leaves of pot-grown wheat seedling
were sprayed to run-off with an aqueous suspension, containing the
concentration of active ingredient or their mixture as described
below. The next day the plants were inoculated with spores of
Puccinia recondite. To ensure the success the artificial
inoculation, the plants were transferred to a humid chamber without
light and a relative humidity of 95 to 99% and 20 to 24.degree. C.
for 24 h. Then the trial plants were cultivated for 6 days in a
greenhouse chamber at 20-24.degree. C. and a relative humidity
between 65 and 70%. The extent of fungal attack on the leaves was
visually assessed as % diseased leaf area. In this test, the plants
which had been treated with 300 ppm of the active substance from
examples I-1, I-2, I-3, I-4, I-5, I-7, I-8, I-9, I-10, I-11, I-12,
I-13 and 1-15, respectively, showed an infection of equal to or
less than 10% whereas the untreated plants were 70% infected.
G4. Preventative fungicidal control of Botritis cinerea on leaves
of green pepper (Botrci P1
[0272] Young seedlings of green pepper were grown in pots to the 4
to 5 leaf stage. These plants were sprayed to run-off with an
aqueous suspension, containing the concentration of active
ingredient or their mixture mentioned in the table below. The next
day the plants were inoculated with a aqueous biomalt solution
containing the spore suspension of Botritis cinerea. Then the
plants were immediately transferred to a humid chamber. After 5
days at 22 to 24.degree. C. and a relative humidity close to 100%
the extent of fungal attack on the leaves was visually assessed as
% diseased leaf area.
Microtest
[0273] The active compounds were formulated separately as a stock
solution having a concentration of 10000 ppm in dimethyl
sulfoxide.
M1. Activity Against Leaf Blotch on Wheat Caused by Septoria
tritici (Septtr)
[0274] The stock solutions were mixed according to the ratio,
pipetted onto a micro titer plate (MTP) and diluted with water to
the stated concentrations. A spore suspension of Septoria tritici
in an aqueous biomalt or yeast-bactopeptone-glycerine solution was
then added. The plates were placed in a water vapor-saturated
chamber at a temperature of 18.degree. C. Using an absorption
photometer, the MTPs were measured at 405 nm 7 days after the
inoculation. The measured parameters were compared to the growth of
the active compound-free control variant (100%) and the fungus-free
and active compound-free blank value to determine the relative
growth in % of the pathogens in the respective active compounds
COMPARISON
TABLE-US-00008 [0275] Disease (%) at Disease (%) at Growth (%) at
Structure 300 pm Septtr P1 300 pm Botrci P1 0.002 ppm Septtr
##STR00025## 30 30 inventive compound I-8, 0 table I inventive
compound I-12, 0 0 table 1 ##STR00026## 40 72 inventive compound
I-7, 0 table I inventive compound I-1, 14 table I unreated control
90 90 --
* * * * *
References